Insecticide for agricultural or horticultural use and method of use thereof

ABSTRACT

An object of the present invention is to provide insecticides having high effectiveness. The present invention provides compounds represented by formula (1):  
                 
 
wherein A 1 , A 2 , A 3 , and A 4  independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R 1  represents a C1-C6 alkyl group which may be substituted, a phenyl group which may be substituted, or a heterocyclic group which may be substituted; R 2  and R 3  independently represent a hydrogen atom, a C1-C4 alkyl group which may be substituted, or a C1-C4 alkylcarbonyl group which may be substituted; G 1 , G 2 , and G 3  independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group which may be substituted, or an amino group which may be substituted; n represents an integer of 0 to 4; Q represents a phenyl group which may be substituted, a naphthyl group which may be substituted, a tetrahydronaphthyl group which may be substituted, or a heterocyclic group which may be substituted, insecticides containing the compounds as active ingredients, and a method for producing the compounds. 
The compounds represented by formula (1) exhibit an excellent preventive effect as insecticides and also exhibit an excellent preventive effect when being combined with another insecticide, an acaricide, a nematocide, a fungicide, a herbicide, a plant growth regulator, or a biological pesticide.

TECHNICAL FIELD

The present invention relates to compounds represented by formula (1), insecticides containing the compounds as active ingredients, a method for producing the insecticides, and a method for using the insecticides.

BACKGROUND ART

PCT Japanese Translation Patent Publication No. 11-511442 discloses salicylic compounds similar to compounds of the present invention. However, compounds represented by formula (1) of the present invention do not have a salicylic skeleton, and the compounds disclosed in the above publication are clearly outside the scope of claims of the present invention.

Publication No. WO2003-22806 discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.

J. Org. Chem. 142 (1966) discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.

J. Am. Chem. Soc. 6382 (2000) discloses compounds as production intermediates similar to the compounds of the present invention, but it does not disclose an activity to insects. Also, the compounds disclosed in the publication are clearly outside the scope of claims of the present invention.

DISCLOSURE OF INVENTION

An object of the present invention is to provide insecticides having high effectiveness.

As a result of intensive research for achieving the object, the inventors found that the compounds of the present invention are novel compounds not disclosed in any document and have an excellent insecticidal effect, and the compounds can be used as new insecticides. It is also found that intermediates in production of the compounds of the present invention are not disclosed in any document and are useful production intermediates. The present invention has been achieved based on these findings.

The present invention provides compounds represented by the following formulae:

[1] Compounds represented by formula (1)

wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₁ represents a C1-C6 alkyl group which may be substituted, a phenyl group which may be substituted, or a heterocyclic group which may be substituted; R₂ and R₃ independently represent a hydrogen atom, a C1-C4 alkyl group which may be substituted, or a C1-C4 alkylcarbonyl group which may be substituted; G₁, G₂, and G₃ independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group which may be substituted, or an amino group which may be substituted; n represents an integer of 0 to 4; Q represents a phenyl group which may be substituted, a naphthyl group which may be substituted, a tetrahydronaphthyl group which may be substituted, or a heterocyclic group which may be substituted.

[2] Compounds represented by formula (1) wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₁ represents the following:

a C1-C6 alkyl group,

a C1-C6 haloalkyl group,

a C2-C6 alkenyl group,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group,

a C2-C6 haloalkynyl group,

a C3-C6 cycloalkyl group,

a C3-C6 halocycloalkyl group,

a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a naphthyl group,

a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group),

a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

-E₁-Z₁-R₄

(wherein E₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group; R₄ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group,

a C3-C8 cycloalkyl group,

a C3-C8 halocycloalkyl group,

a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a naphthyl group,

a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or

a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group), and

Z₁ represents —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R₅)—, —C(═O)N(R₅)—, or —N(R₅)C(═O)— (R₅ represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, or a C1-C4 alkoxycarbonyl group)), or -E₂-R₆

(wherein E₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, and R₆ represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,

a cyano group,

a nitro group,

a hydroxyl group,

a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a naphthyl group,

a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group,

a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or

a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group);

R₂ and R₃ independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G₁, G₂, and G₃ independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, an amino group, or an amino group which may be substituted by a C1-C4 alkyl group;

n represents an integer of 0 to 4;

Q represents a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a phenyl group, a substituted phenyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a thienyl group, and a substituted thienyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group),

a naphthyl group,

a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a tetrahydronaphthyl group, or

a substituted tetrahydronaphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group (excluding a case (1) in which Q represents 3,4-dichlorophenyl when R1 represents a methyl group, a case (2) in which Q represents an unsubstituted phenyl group when R1 represents an ethyl group, and a case (3) in which Q represents an unsubstituted pyridyl group when R1 represents an unsubstituted phenyl group).

[3] Compounds represented by formula (2)

wherein A₁, A₂, A₃, A₄, R₁, R₂, R₃, G₁, G₂, G₃, X, and n each represent the same as in formula [1], and Hal represents a halogen atom.

[4] Compounds represented by formula (3)

wherein A₁, A₂, A₃, A₄, R₃, G₃, X, n and Q each represent the same as in formula [1].

[5] Compounds represented by formula (4)

wherein A₁, A₂, A₃, A₄, R₂, R₃, G₃, X, and n each represent the same as in formula [1], and Q represents a group represented by formula (1-2) or (1-3):

(wherein Y₁, Y₂, Y₄, and Y₅ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₃ represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₁ and Y₅ represents a hydrogen atom)

(wherein Y₆, Y₇, and Y₉ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₈ represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₆ and Y₉ represents a hydrogen atom).

[6] A method for producing the above-described compounds in [1] comprising reacting the compounds represented in [3] by formula (2) with compounds represented by formula (5):

wherein R₃ and Q each represent the same as in [1].

[7] A method for producing the above-described compounds in [1] comprising reacting the compounds represented in [4] by formula (3) with compounds represented by formula (6): H-G₂-R  (6) wherein R₁ and G₂ each represent the same as in [1].

[8] A method for producing the above-described compounds in [1] comprising reacting the compounds represented in [5] by formula (4) with compounds represented by formula (7):

wherein R₁, G₁, and G₂ each represent the same as in [1]

[9] Aniline derivatives represented by formula (8):

wherein R₇ represents a C1-C6 haloalkyl group, Y₁₀, Y₁₁, Y₁₂, and Y₁₃ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and R₈ and R₉ independently represent a hydrogen atom, a C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted m-nitrobenzoyl group, and m represents 0, 1, or 2.

[10] Aniline derivatives represented by formula (9):

wherein R₁₀ represents a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, Y₁₄, Y₁₅, Y₁₆, and Y₁₇ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and R₁₁, and R₁₂ independently represent a hydrogen atom, a C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted m-nitrobenzoyl group.

[11] An insecticide comprising any one of the compounds in [1] or [2] as an active ingredient.

[12] A method for using a chemical comprising treating a useful crop or soil with an effective amount of any one of the compounds [1] or [2], for protecting the useful crop from harmful organisms.

[13] A method for preventing pests comprising using the compound [1] or [2] and at least one insecticide and/or fungicide in combination.

The compounds of the present invention exhibit an excellent preventive effect as insecticides in low dosages, and also exhibit an excellent preventive effect when being used in combination with another insecticide, an acaricide, a nematocide, a fungicide, a herbicide, a plant growth regulator, or a biological pesticide.

BEST MODE FOR CARRYING OUT THE INVENTION

In the definitions of formula (1) of the present invention, the term “halogen atom” means a fluorine atom, a chlorine, atom, a bromine atom, or an iodine atom. The characters “n-”, “i-”, “s-”, and “t-” mean “normal”, “iso”, “secondary”, and “tertiary”, respectively. With respect to the expression “Ca-Cb (a and b each represent an integer of 1 or more)”, for example, “C1-C6” means that the number of carbon atoms is 1 to 6, “C3-C8” means that the number of carbon atoms is 3 to 8, and “C1-C4” means that the number of carbon atoms is 1 to 4.

In the definitions of the formulae such as formula (1) of the present invention, the used terms have the following meanings:

The term “an alkyl group which may be substituted” means a straight, branched or cyclic alkyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “an alkylcarbonyl group which may be substituted” means a straight, branched or cyclic alkylcarbonyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “a phenyl group which may be substituted” means a phenyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “a naphthyl group which may be substituted” means a naphthyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “a tetrahydronaphthyl group which may be substituted” means a tetrahydronaphthyl group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “a heterocyclic group which may be substituted” means a heterocyclic group which may be substituted by the same or different groups selected from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a phenyl group which may be substituted, a phenylcarbonyl group which may be substituted, a phenylamino group which may be substituted, and a heterocyclic group which may be substituted.

The term “a C1-C6 alkyl group” means a straight or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, 2-pentyl, neopentyl, 4-methyl-2-pentyl, n-hexyl, or 3-methyl-n-pentyl. The term “a C1-C6 haloalkyl group” means a straight or branched alkyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-1-propyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1-trifluoro-2-propyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 3,3,3-trifluoro-n-propyl, 4,4,4-trifluoro-n-butyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-bromo-2-propyl, 1,1,2,3,3,3-hexafluoro-2-chloro-n-propyl, 1,1,2,3,3,3-hexafluoro-2-bromo-n-propyl, 1,1,2,3,3,3-hexafluoro-1-bromo-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, 3,3,4,4,4-pentafluoro-2-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, or 3-bromo-n-propyl.

The term “a C2-C6 alkenyl group” means an alkenyl group having 2 to 6 carbon atoms and a double bond in its carbon chain, such as vinyl, allyl, 2-butenyl, or 3-butenyl. The term “a C2-C6 haloalkenyl group” means a straight or branched alkenyl group having 2 to 6 carbon atoms and a double bond in its carbon chain and substituted by one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, or 3,4,4-tribromo-3-butenyl.

The term “a C2-C6 alkynyl group” means an alkynyl group having 2 to 6 carbon atoms and a triple bond in its carbon chain, such as propargyl, 1-butyne-3-yl, or 1-butyne-3-methyl-3-yl. The term “a C2-C6 haloalkenyl group” means a straight or branched alkyenyl group having 2 to 6 carbon atoms and a triple bond in its carbon chain and substituted by one or more halogen atoms which may be the same or different.

The term “a C3-C8 cycloalkyl group” means a cycloalkyl group having 3 to 8 carbon atoms and a cyclic structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, or 4-methylcyclohexyl. The term “a C3-C8 halocycloalkyl group” means a cycloalkyl group having 3 to 8 carbon atoms and a cyclic structure and substituted by one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, or 4-chlorocyclohexyl.

The term “a C1-C6 alkoxy group” means a straight or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, s-butoxy, i-butoxy, or t-butoxy. The term “a C1-C6 haloalkoxy group” means a straight or branched haloalkoxy group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethoxy, pentafluoroethoxy, heptafluoro-n-propyloxy, heptafluoro-1-propyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, or 3-fluoro-n-propyloxy.

The term “a C1-C6 alkylthio group” means a straight or branched alkylthio group having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, s-butylthio, or t-butylthio. The term “a C1-C6 haloalkylthio group” means a straight or branched alkylthio group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-1-propylthio, nonafluoro-n-butylthio, or nonafluoro-2-butylthio.

The term “a C1-C6 alkylsulfinyl group” means a straight or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, s-butylsulfinyl, or t-butylsulfinyl. The term “a C1-C6 haloalkylsulfinyl group” means a straight or branched alkylsulfinyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, or nonafluoro-2-butylsulfinyl.

The term “a C1-C6 alkylsulfonyl group” means a straight or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, s-butylsulfonyl, or t-butylsulfonyl. The term “a C1-C6 haloalkylsulfonyl group” means a straight or branched alkylsulfonyl group having 1 to 6 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, or nonafluoro-2-butylsulfonyl.

The term “a C1-C4 alkylcarbonyl group” means a straight, branched, or cyclic alkylcarbonyl group having 1 to 4 carbon atoms, such as acetyl, propionyl, isopropylcarbonyl, or cyclopropylcarbonyl. The term “a C1-C4 haloalkylcarbonyl group” means a straight or branched alkylcarbonyl group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoroacetyl, pentafluoropropionyl, trichloroacetyl, chloroacetyl, bromoacetyl, or 3-chloropropionyl.

The term “a C1-C4 alkoxycarbonyl group” means a straight or branched alkoxycarbonyl group having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, or isopropyloxycarbonyl.

The term “a C1-C4 alkylcarbonyloxy group” means a straight or branched alkylcarbonyloxy group having 1 to 4 carbon atoms, such as acetoxy or propionyloxy. The term “a C1-C4 alkylsulfonyloxy group” means a straight or branched alkylsulfonyloxy group having 1 to 4 carbon atoms, such as methylsulfonyloxy. The term “a C1-C4 haloalkylsulfonyloxy group” means a straight or branched alkylsulfonyloxy group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyloxy or pentafluoroethylsulfonyloxy.

The term “a C1-C4 alkylene group” means a straight or branched alkylene group having 1 to 4 carbon atoms, such as methylene, ethylene, propylene, dimethylmethylene, or isobutylene. The term “a C2-C4 alkenylene group” means a straight or branched alkenylene group having 2 to 4 carbon atoms and a double bond in its carbon chain. The term “a C3-C4 alkynylene group” means a straight or branched alkynylene having 3 to 4 carbon atoms and a triple bond in its carbon chain. The term “a C1-C4 haloalkylene group” means a straight or branched alkylene group having 1 to 4 carbon atoms and substituted by one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, or difluoromethylene.

The term “a C2-C4 haloalkenylene group” means a straight or branched alkynylene having 2 to 4 carbon atoms and a double bond in its carbon chain, and substituted by one or more halogen atoms which may be the same or different. The term “a C3-C4 haloalkynylene group” means a straight or branched alkynylene group having 3 to 4 carbon atoms and a triple bond in its carbon chain, and substituted by one or more halogen atoms which may be the same or different.

The term “a C1-C6 haloalkyl group which may be substituted by one ore more hydroxyl groups” means a straight or branched alkyl group having 1 to 6 carbon atoms and one or more hydroxyl groups in its carbon chain, and substituted by one or more halogen atoms which may be the same or different, such as 1,2,2,2-tetrafluoro-1-hydroxyethyl, 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl, 1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl, 1,2,2,3,3,4,4,4-octafluoro-1-hydroxy-n-butyl, or 1,3-dichloro-1,1,3,3-tetrafluoro-2-hydroxy-2-propyl.

The term “a substituted m-nitrobenzoyl group” means a m-nitrobenzoyl group having one or more substituents, such as 2-fluoro-3-nitrobenzoyl, 4-fluoro-3-nitrobenzoyl, 2-fluoro-5-nitrobenzoyl, or 4-chloro-3-nitrobenzoyl.

The compounds represented by formula (1) of the present invention may contain at least one asymmetric carbon atom or asymmetric center and thus have at least two types of optical isomers. The present invention includes the optical isomers and mixtures thereof at any proportions. The compounds represented by formula (1) of the present invention may contain at least two types of geometric isomers derived from carbon-carbon double bonds in the structural formulae. The present invention also includes the geometric isomers and mixtures thereof at any proportions.

Preferred examples of the substituents or atoms in the compounds represented by the formulae such as formula (1) of the present invention include the following:

Preferably, R₁ is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, a C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, -E₁-Z₁-R₄ (wherein E₁ represents C1-C4 alkylene, C2-C4 alkenylene, C3-C4 alkynylene, C1-C4 haloalkylene, C2-C4 haloalkenylene, or C3-C4 haloalkynylene, R₄ represents a hydrogen atom, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, or C2-C6 haloalkynyl, and Z₁ represents —O—, —S—, —SO—, or —SO₂—), or -E₂-R₆ (wherein E₂ represents C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, or C3-C4 haloalkynyl, and R₆ represents C3-C8 cycloalkyl, C3-C8 halocycloalkyl, cyano, nitro, hydroxyl, phenyl, substituted phenyl having one or more substituents which may be the same or different and which are selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, cyano, nitro, hydroxyl, C1-C4 alkylcarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkylcarbonyloxy, and C1-C4 alkoxycarbonyl, pyridyl, or substituted pyridyl having one or more substituents selected from halogen, C1-C6 haloalkyl, and C1-C6 haloalkoxy). More preferably, R₁ is C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl, -E₁-Z₁-R₄ (wherein E₁ represents C1-C4 alkylene or C1-C4 haloalkylene, R₄ represents C1-C6 alkyl or C1-C6 haloalkyl, and Z₁ represents —O—, —S—, —SO—, or —SO₂—), or -E₂-R₆ (wherein E₂ represents C1-C4 alkyl, R₆ represents C3-C8 cycloalkyl, cyano, substituted phenyl having one or more substituents which may be the same or different and which are selected from halogen, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, cyano, and nitro, pyridyl, substituted pyridyl having one or more substituents selected from halogen, C1-C6 haloalkyl, and C1-C6 haloalkoxy, thienyl, or tetrahydrofuryl).

Preferably, R₂ and R₃ are independently hydrogen or C1-C4 alkyl, and more preferably hydrogen, methyl, or ethyl.

Preferably, G₁, G₂, and G₃ are independently oxygen or sulfur, and more preferably oxygen.

Preferably, X is hydrogen, halogen or trifluoromethyl, and more preferably hydrogen or fluorine.

Preferably, n is 0 or 1.

Preferably, Q is phenyl, substituted phenyl having one or more substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, pentafluorosulfanyl, cyano, and nitro, pyridyl, or substituted pyridyl having one or more substituents selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, pentafluorosulfanyl, cyano, and nitro. More preferably, Q is substituted phenyl or substituted pyridyl represented by formula (1-2) or (1-3). In the formula, preferably, Y₁ and Y₅ are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of Y₁ and Y₅ represents a hydrogen atom.

Preferably, Y₂ and Y₄ are each hydrogen.

Preferably, Y₃ is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y₃ is C1-C6 haloalkyl, C1-C6 haloalkyl which may be substituted by one or more hydroxyl group, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, or C1-C6 haloalkylsulfonyl.

Preferably, Y₆ and Y₉ are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of Y₆ and Y₉ represents a hydrogen atom.

Preferably, Y₇ is hydrogen.

Preferably, Y₈ is C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkyl which may be substituted by one or more hydroxyl groups, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, or pentafluorosulfanyl. More preferably, Y₈ is C1-C6 haloalkyl or C1-C6 haloalkoxy.

Preferably, Hal is chlorine.

Preferably, R₇ is C1-C6 haloalkyl, and more preferably R₇ is C1-C6 alkyl substituted by fluorine, such as pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, or nonafluoro-2-butyl.

Preferably, Y₁₀ and Y₁₃ are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of Y₁₀ and Y₁₃ represents a hydrogen atom. More preferably, Y₁₀ and Y₁₃ are each chlorine, bromine, or methyl.

Preferably, Y₁₁, and Y₁₂ are each hydrogen.

Preferably, R₈ and R₉ are each hydrogen, C1-C4 alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl, and only one of R₈ and R₉ represent C1-C4 alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl.

Preferably, m is 0, 1, or 2.

Preferably, R₁₀ is 1,2,2,2-tetrafluoro-1-hydroxyethyl, 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl, 1,1,1,3,3,4,4,4-octafluoro-2-hydroxy-2-butyl, 1,2,2,3,3,4,4,4-octafluoro-1-hydroxy-n-butyl, or 1,3-dichloro-1,1,3,3-tetrafluoro-2-hydroxy-2-propyl, and more preferably, R₁₀ is 1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl.

Preferably, Y₁₄ and Y₁₇ are independently hydrogen, C1-C4 alkyl, halogen, or methylthio, and only one of Y₁₄ and Y₁₇ represents a hydrogen atom. More preferably, none of Y₁₄ and Y₁₇ represents a hydrogen atom.

Preferably, Y₁₅ and Y₁₆ are each hydrogen.

Preferably, R₁₁ and R₁₂ are each hydrogen, C1-C4 alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl, and only one of R₁₁ and R₁₂ represents C1-C4 alkyl, m-nitrobenzoyl, or 2-fluoro-3-nitrobenzoyl.

Representative processes for producing the compounds of the present invention will be described below. Although the compounds of the present invention can be produced according to the methods, the production processes are not limited to the processes described below.

An embodiment of the representative processes for producing the compounds of the present invention is Production Method 1 (in the formula, R₁, R₃, G₁, G₂, (X)n, and Q represent the same as described above).

1-(i) Formula (10) →Formula (12)

A m-nitrobenzoyl chloride derivative represented by formula (10) is reacted with an aromatic amine derivative represented by formula (11) in an appropriate solvent to produce a benzamide derivative represented by formula (12). In this step, an appropriate base can also be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (10). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. The m-nitrobenzoyl chloride derivative represented by formula (10) can be easily produced from a m-nitrobenzoic acid derivative by a conventional method using a halogenating agent. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride. In a process for producing the compound represented by formula (12) using the m-nitrobenzoic acid derivative and the compound represented by formula (11) without using a halogenating agent, 1-hydroxybenzotriazole functioning as an additive, and N,N′-dicyclohexyl carbodiimide functioning as a condensing agent can be used according to the technique disclosed in, for example, Chem. Ber. p. 788 (1970). Other examples of the condensing agent include 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and 1,1′-carbonyl-bis-1H-imidazole. Alternatively, the compound represented by formula (12) can be produced by a mixed acid anhydride technique using a chloroformic acid ester according to the technique disclosed in J. Am. Chem. Soc. p. 5012 (1967). Examples of the chloroformic acid ester include isobutyl chloroformate and isopropyl chloroformate. Instead of the chloroformic acid ester, diethylacetyl chloride or trimethylacetyl chloride can be used. In the technique using the condensing agent and the mixed acid anhydride technique, the solvent, the reaction temperature, and the reaction time are not limited to those disclosed in the above documents, and an inert solvent which does not inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction.

1-(ii) Formula (12) →Formula (13)

The benzamide derivative having a nitro group represented by formula (12) can be converted to a benzamide derivative having an amino group represented by formula (13) by reduction reaction. Examples of a technique for the reduction reaction include a technique using hydrogenation and a technique using tin(II) chloride (anhydride). In the former technique, reaction can be performed in a hydrogen atmosphere in the presence of a catalyst in a proper solvent under normal pressure or high pressure. Examples of the catalyst include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, and platinum catalysts. Examples of the solvent include water, alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene and toluene; chained or cyclic ethers such as ethers, dioxane, and tetrahydrofuran; and esters such as ethyl acetate. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. As a result, the compound represented by formula (13) can be produced. In the latter technique, the conditions are not limited, and the compound represented by formula (13) can be produced under the conditions described in, for example, Organic Syntheses, Coll. Vol. III, p. 453.

1-(iii) Formula (13) →Formula (14)

The benzamide derivative having a amino group represented by formula (13) is reacted with a compound represented by formula (7) (for example, a chloroformic ester, a chlorothioformic ester, or a chlorodiformic thioester) in a proper solvent to produce a compound represented by formula (14) of the present invention. In this step, an appropriate base can also be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, and 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (13). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

A compound represented by formula (16) of the present invention can be produced by Production Method 2 (in the formula, R₁, R₃, G₂, (X)n, and Q represent the same as described above) using a 3-isocyanatobenzoly chloride represented by formula (15) as a starting material, an alcohol represented by formula (6), a thiol, and an aromatic amine represented by formula (11) according to the technique disclosed in J. Org. Chem., p. 142 (1966).

In this step, a solvent can be used. As the solvent, any solvent other than the solvents described in the above document can be used as long as it does not significantly inhibit the progress of reaction. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating the reaction. Examples of the base other than those disclosed in the above document include organic bases such as triethylamine, pyridine, and 4-dimethylaminopyridine; and inorganic bases such as potassium carbonate. The base may be used in an appropriate amount in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (15). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

A thioamide compound can be produced from a compound represented by formula (17) using a Lawson reagent according Production Method 3 (in the formula, R₁, R₂, R₃, G₁, G₂, (X)n, and Q represent the same as described above).

3-(i) Formula (17) →Formula (18)

The reaction can be performed under the conditions described in Synthesis, p. 463 (1993) and Synthesis, p. 829 (1984), but the conditions such as a solvent are not limited to those described in these documents.

3-(ii) Formula (18) →Formula (19)

A compound represented by formula (19) of the present invention can be produced using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions properly selected from the reaction conditions described above in the step 1-(iii) of Production Method 1.

A chloropyridinecarboxylic acid can be used as a starting material. For example, a compound represented by formula (23) can be produced from a chloropyridinecarboxylic acid represented by formula (20) according to Production Method 4 (in the formula, R₁, R₂, R₃, Q, G₁, and G₂ represent the same as described above)

4-(i) Formula (20) →Formula (21)

A compound represented by formula (18) is halogenated in the presence or absence of an inert solvent and then reacted with an aromatic amine represented by formula (11) to produce a compound represented by formula (21). As the solvent usable in the halogenation step, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Examples of a halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride. The amount of the halogenating agent used may be appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound represented by formula (20). Also, N,N-dimethylformamide may be added as an auxiliary for accelerating the reaction. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. As the solvent usable in the amidation step, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating the progress of reaction. Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine; and inorganic bases such as potassium carbonate. The amount of the base used may be appropriately determined in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (11). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

A process for producing a compound represented by formula (21) from a compound represented by formula (20) and a compound represented by formula (11) without using a halogenating agent is presented by a process according to the technique disclosed in, for example, Chem. Ber., p. 788 (1970) where 1-hydroxybenzotriazole as an additive and N,N′-dicyclohexyl carbodiimide as a condensing agent are used, respectively. Other examples of the condensing agent include 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide, and 1,1′-carbonyl-bis-1H-imidazole. The compound represented by formula (21) can also be produced by a mixed acid anhydride technique using a chloroformic ester according to the technique disclosed in J. Am. Chem. Soc., p. 5012 (1967). Examples of a chloroformic ester include isobutyl chloroformate and isopropyl chloroformate. A compound other than a chloroformic ester, for example, diethylacetyl chloride or trimethylacetyl chloride, can also be used. In the technique using the condensing agent and the mixed acid anhydride technique, the solvent, the reaction temperatures, and the reaction times are not limited to those disclosed in the above documents, and an inert solvent which does not significantly inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction.

4-(ii) Formula (21) →Formula (22)

A compound represented by formula (22) can be produced by amination with ammonia according to the conditions described in, for example, J. Org. Chem., p. 280 (1958). The conditions such as the reaction solvent are not limited to those disclosed in the above document, and an inert solvent which does not significantly inhibit the progress of reaction may be appropriately used. Also, the reaction temperature and the reaction time may be appropriately selected according to the progress of reaction. As an aminating agent, methylamine or ethylamine can be used instead of ammonia.

4-(iii) Formula (22) →Formula (23)

A compound represented by formula (23) of the present invention can be produced by using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions appropriately selected from the reaction conditions described above in the step

1-(iii) of Production Method 1.

Even when another nitrogen-containing aromatic carboxylic acid such as 4-chloropyridine-2-carboxlic acid or 6-chloropyridine-2-carboxylic acid is selected as a starting material, the compound of the present invention can be produced according to Production Method 4. In the use of the former starting material, a compound represented by formula (1) wherein A₁ is a nitrogen atom, and A₂, A₃, and A₄ are each a carbon atom can be produced. In the use of the latter starting material, a compound represented by formula (1) wherein A₁, A₂, and A₃ are each a carbon atom, and A₄ is a nitrogen atom can be produced.

The compound represented by formula (23) is reacted with an appropriate oxidizing agent to produce a corresponding pyridine-N-oxide derivative according to the conditions disclosed in, for example, J. Org. Chem., p. 8576 (1999). Examples of the oxidizing agent include organic peroxy acids such as m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen peroxide; ozone; selenium dioxide, chromic acid; dinitrogen tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide; iodosylbenzene; and t-butyl hypochlorite. The solvent used in this step is not limited to those disclosed in the above document, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

A compound represented by formula (27) of the present invention can be produced from a easily available m-aminobenzoic ester derivative presented by formula (24) according to Production Method 5 (in the formula, R₁, R₂, R₃, G₁, G₂, (X)n, and Q represent the same as described above, and R represents a lower alkyl group).

5-(i) Formula (24) →Formula (25)

A compound represented by formula (25) can be produced by using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under the conditions appropriately selected from the reaction conditions described above in the step 1-(iii) of Production Method 1.

5-(ii) Formula (25) →Formula (26)

A compound represented formula (26) can be produced by hydrolysis with an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkali earth metal hydroxide such as calcium hydroxide, or an inorganic acid such as hydrochloric acid or sulfuric acid according to a conventional technique.

5-(iii) Formula (26) →Formula (27)

A compound represented by formula (27) of the present invention can be produced by condensation reaction under appropriate conditions according to the technique described above in the step 4-(i) of Production Method 4. Among the techniques described in the step 4-(i), in the technique using a halogenating agent, the compound represented by formula (27) can be produced through a compound represented by formula (2):

(wherein A₁, A₂, A₃, A₄, G₁, G₂, G₃, (X)n, and Hal each represent the same as described above). The halogenation step and the amidation step can be performed under reaction conditions according to the technique described above in the step 4-(i).

The compound represented by formula (27) of the present invention can be produced from a m-aminobenzoic acid ester represented by formula (28) according to Production Method 6 below (in the formula, R₁, R₂, R₃, G₁, G₂, (X)n, and Q each represent the same as described above, R represents a lower alkyl group, and L represents a functional group having leaving ability, such as halogen, methanesulfonyloxy, or trifluoromethanesulfonyloxy).

6-(i) Formula (28) →Formula (29)

A compound represented formula (29) can be produced by the technique described above in the step 1-(iii) of Production Method 1 using a compound represented by formula (7) (for example, a chloroformic ester or a chlorothioformic ester) under appropriate conditions.

6-(ii) Formula (29) →Formula (25)

In this step, examples of a compound represented by formula (30) include alkyl halides such as methyl iodide and ethyl iodide; toluenesulfonic esters; methanesulfonic esters; and alkylating agents such as dimethyl sulfate. As a solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, a base may be added for accelerating the progress of reaction. Examples of the base include organic bases such as triethylamine, pyridine, and 4-dimethylaminopyridine; inorganic bases such as potassium carbonate, sodium hydroxide, and potassium hydroxide; and alkali metal hydrides such as sodium hydride. The amount of the base used may be appropriately determined in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (29). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

6-(iii) Formula (25) →Formula (27)

A compound represented by formula (27) of the present invention can be produced by the techniques described above in the steps 5-(ii) and 5-(iii) of Production Method 5 under appropriate conditions.

A compound represented by formula (31) of the present invention can be produced according to Production Method 7 (in the formula, A₁, A₂, A₃, A₄, R₁, R₃, G₂, G₃, and (X)n each represent the same as described above).

In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. Also, an appropriate base may be used. Examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. The amount of the base used may be appropriately determined in the range of molar equivalents of 0.01 to 5 times the amount of the compound represented by formula (6). The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

An isocyanate compound represented by formula (3) can be produced by Production Method 8 (in the formula, A₁, A₂, A₃, A₄, G₃, R₃, (X)n, and Q each represent the same as described above) using a m-aminobenzamide derivative or a m-aminopyridinecarboxamide derivative represented by formula (32) as a starting material.

In this step, reaction can be performed by using phosgene according to the technique described in Organic Syntheses, Coll., Vol. II, p. 453. An isocyanate compound represented by formula (3) can also be produced by using a phosgene dimmer, triphosgene, or oxalyl chloride instead of phosgene. In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

An isocyanate compound represented by formula (3) can also be produced by Production Method 9 (in the formula, A₁, A₂, A₃, A₄, G₃, R₃, (X)n, and Q each represent the same as described above) utilizing Curtius rearrangement reaction with an isophthaloyl chloride derivative represented by formula (33) used as a starting material according to the technique described in Macromolecules, p. 1046 (1998).

In this step, an appropriate solvent may be used. As the solvent, any solvent which does not significantly inhibit the progress of reaction can be used. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents can be used alone or in a mixture of two ore more kinds. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours. In producing a compound represented formula (34), ethanol, propanol, or benzyl alcohol can be used as an alcohol. In esterolysis, hydrolysis or catalytic hydrogen reduction can be performed by a conventional technique.

An aniline derivative represented by formula (39) can be produced by using an aminothiophenol derivative as a starting material according Production Method 10 (in the formula, R₇, Y₁₁, Y₁₂, and m each represent the same as described above, Y₁₀ and Y₁₃ each represent a hydrogen atom or a halogen atom except a case in which both groups are hydrogen atoms as far as this Method is concerned, Y_(10a) and Y_(13a) each represent a hydrogen atom, a halogen atom, or a methyl group as far as this Method is concerned, and one of Y_(10a) and Y_(13a) necessarily represents a methyl group).

10-(i) Formula (35) →Formula (37)

A compound represented by formula (38) can be produced by reaction of aminothiophenol represented by formula (35) with a haloalkyl iodide represented by formula (36) according to the method described in J. Fluorine Chem., p. 207 (1994).

Examples of a haloalkyl iodide represented by formula (36) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-butyl iodide, and nonafluoroisopropyl iodide. The amount of the haloalkyl iodide used may be appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound represented formula (35). The solvent used in this step is not limited to those described in the above document, and any solvent which does not significantly inhibit the progress of reaction can be used as the solvent. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide. These solvents can be used alone or in a mixture of two ore more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of −20° C. to the reflex temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

10-(ii) Formula (37) →Formula (38)

A compound represented by formula (38) can be produced by using an appropriate halogenating agent according to the technique described in, for example, Synth. Commun., p. 1261 (1989). Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. The amount of the halogenating agent used may be appropriately determined in the range of molar equivalents of 1 to 10 times the amount of the compound represented formula (37). The number of equivalents of the halogenating agent used can be appropriately determined so that only Y₁₀ or Y₁₃ is a halogen atom. In this step, an appropriate solvent may be used. The solvent used is not limited to those described in the above document, and any solvent which does not significantly inhibit the progress of reaction can be used as the solvent. Examples of the solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; ketones such as acetone, methyl isobutyl ketone, and cyclohexanone; amides such as dimethylformamide and dimethylacetamide; nitrites such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide. These solvents can be used alone or in a mixture of two ore more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

10-(iii) Formula (38) →Formula (39)

A compound represented by formula (39) can be produced by using an appropriate oxidizing agent according to the technique described in, for example, Tetrahedron Lett., p. 4955 (1994). Examples of the oxidizing agent include organic peroxy acids such as m-chloroperoxybenzoic acid; sodium metaperiodate; hydrogen peroxide; ozone; selenium dioxide, chromic acid; dinitrogen tetraoxide; acyl nitrate; iodine; bromine; N-bromosuccinimide; iodosylbenzene; and t-butyl hypochlorite. The solvent used in this step is not limited to those disclosed in the above document, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. In particular, a polar solvent is preferred. The reaction temperature may be appropriately determined in the range of −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

10-(iv) Formula (38) →Formula (38-2)

A compound represented by formula (38-2) (wherein R₇, Y₁₁, Y₁₂, and m each represent the same as described above, Y_(10a) and Y_(13a) each represent a hydrogen atom, a halogen atom, or a methyl group as far as this step is concerned, and one of Y_(10a) and Y_(13a) necessarily represents a methyl group) can be produced from the compound represented by formula (38) using an appropriate methylating agent. This step can be performed according to the technique described in, for example, Tetrahedron. Lett., p. 6237 (2000).

10-(v) Formula (38-2) →Formula (39-2)

A compound represented by formula (39-2) (wherein R₇, Y₁₁, Y₁₂, and m each represent the same as described above, Y_(10a) and Y_(13a) both represent a methyl group or one of Y_(10a) and Y_(13a) represents a methyl group and the other represents a halogen atom as far as this step is concerned) can be produced according to the technique descried above in the step 10-(iii) of Production Method 10.

The compounds represented by formula (1), (3), (4), and (8) can be produced from aniline derivatives represented by formula (38), (39), (38-2) and (39-2) according to any one Method appropriately selected from Production Methods 1 to 9.

The compound represented by formula (39) can also be produced from an aminothiophenol represented by formula (40) according to Production Method 11 (in the formula, R₇, Y₁₀, Y₁₁, Y₁₂, Y₁₃, and m each represent the same as described above).

Reaction with a haloalkyl iodide and subsequent oxidation can be performed according to Production Method 10. The compounds represented by formula (1), (3), (4), and (8) can be produced from aniline derivatives represented by formula (41) and (42) according to any one Method appropriately selected from Production Methods 1 to 9.

A compound represented by formula (9) can also be produced from an aniline derivative represented by formula (41) and used as a starting material according to Production Method 12 (in the formula, R₁₀, R₁₁, R₁₂, Y₁₄, Y₁₅, Y₁₆, and Y₁₇ each represent the same as described above).

A compound represented by formula (9) can be produced by using an appropriate perfluorinated aldehyde or perfluorinated ketone according to the technique described in, for example, J. Am. Chem. Soc., p. 2410 (1965) and J. Org. Chem., p. 1001 (1965). Examples of the perfluorinated aldehyde or perfluorinated ketone include hexafluoroacetone and perfluoro-2-butanone. In this step, an appropriate solvent can be used. The solvent used in this step is not limited to those disclosed in the above documents, and any solvent which does not significantly inhibit the progress of reaction may be used. The solvents can be used alone or in a mixture of one or more kinds. The reaction temperature may be appropriately determined in the range of −20° C. to 200° C., and the reaction time may be appropriately determined in the range of several minutes to 96 hours.

The compounds represented by formula (1), (3), and (4) can be produced from an aniline derivative represented by formula (9) according to any one properly selected from Production Methods 1 to 9.

In all the production Methods, the compounds may be isolated from the reaction systems after reactions according to a normal technique. However, the compounds can be optionally purified by an operation such as recrystallization, column chromatography, distillation, or the like. Alternatively, the compounds may be used in next reaction steps without being isolated from the reaction systems.

Although typical examples of the compounds represented by formula (1) and used as active ingredients of insecticides of the present invention are shown in Tables 1 to 5, the present invention is not limited to these examples.

Although typical examples of the compounds represented by formula (4) are shown in Tables 6 to 8, the present invention is not limited to these examples.

In the tables, “n-” denotes normal, “Me” denotes a methyl group, “Et” denotes an ethyl group; “n-Pr” denotes a normal propyl group, “i-Pr, denotes an isopropyl group, “n-Bu” denotes a normal butyl group, “i-Bu” denotes an isobutyl group, “s-Bu” denotes a secondary butyl group, “t-Bu” denotes a tertiary butyl group, “H” denotes a hydrogen atom, “O” denotes an oxygen atom, “S” denotes a sulfur atom, “C” denotes a carbon atom, “N” denotes a nitrogen atom, “F” denotes a fluorine atom, “Cl” denotes a chlorine atom, “Br” denotes a bromine atom, “I” denotes an iodine atom, “CF₃” denotes a trifluoromethyl group, “MeO” denotes a methoxy group, “NH₂” denotes an amino group, “MeNH” denotes a methylamino group, and “Me₂N” denotes a dimethylamino group. TABLE 1 (1-A)

Compound No. R₁ Q 1 Me 2-methyl-4-heptafluoroisopropylphenyl 2 Et 2-methyl-4-heptafluoroisopropylphenyl 3 i-Pr 2-methyl-4-heptafluoroisopropylphenyl 4 n-Bu 2-methyl-4-heptafluoroisopropylphenyl 5 i-Bu 2-methyl-4-heptafluoroisopropylphenyl 6 s-Bu 2-methyl-4-heptafluoroisopropylphenyl 7 t-Bu 2-methyl-4-heptafluoroisopropylphenyl 8 neopentyl 2-methyl-4-heptafluoroisopropylphenyl 9 3,3-dimethyl-n-butyl 2-methyl-4-heptafluoroisopropylphenyl 10 2-ethyl-n-hexyl 2-methyl-4-heptafluoroisopropylphenyl 11 vinyl 2-methyl-4-heptafluoroisopropylphenyl 12 allyl 2-methyl-4-heptafluoroisopropylphenyl 13 2-isopropyl-5-methylcyclohexyl 2-methyl-4-heptafluoroisopropylphenyl 14 benzyl 2-methyl-4-heptafluoroisopropylphenyl 15 3-cyanobenzyl 2-methyl-4-heptafluoroisopropylphenyl 16 4-cyanobenzyl 2-methyl-4-heptafluoroisopropylphenyl 17 2-methoxyethyl 2-methyl-4-heptafluoroisopropylphenyl 18 chloromethyl 2-methyl-4-heptafluoroisopropylphenyl 19 2-chloroethyl 2-methyl-4-heptafluoroisopropylphenyl 20 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 21 1,2,2,2-tetrachloroethyl 2-methyl-4-heptafluoroisopropylphenyl 22 1,1-dimethyl-2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 23 3-trifluoromethylphenyl 2-methyl-4-heptafluoroisopropylphenyl 24 4-methylphenyl 2-methyl-4-heptafluoroisopropylphenyl 25 4-chlorophenyl 2-methyl-4-heptafluoroisopropylphenyl 26 cyclobutyl 2-methyl-4-heptafluoroisopropylphenyl 27 cyclopentyl 2-methyl-4-heptafluoroisopropylphenyl 28 2-cyanoethyl 2-methyl-4-heptafluoroisopropylphenyl 29 2-(ethylthio)ethyl 2-methyl-4-heptafluoroisopropylphenyl 30 2-(ethylsulfinyl)ethyl 2-methyl-4-heptafluoroisopropylphenyl 31 2-(ethylsulfonyl)ethyl 2-methyl-4-heptafluoroisopropylphenyl 32 2-fluoroethyl 2-methyl-4-heptafluoroisopropylphenyl 33 2,2-difluoroethyl 2-methyl-4-heptafluoroisopropylphenyl 34 2,2,2-trifluoroethyl 2-methyl-4-heptafluoroisopropylphenyl 35 1,3-difluoro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl 36 1-chloro-3-fluoro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl 37 1-methyl-2,2,2- 2-methyl-4-heptafluoroisopropylphenyl trifluoro-2-propyl 38 3,3,3-trifluoro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 39 3,3,4,4,4-pentafluoro-2-butyl 2-methyl-4-heptafluoroisopropylphenyl 40 4,4,4-trifluoro-n-butyl 2-methyl-4-heptafluoroisopropylphenyl 41 2,2,3,3-tetrafluorocyclobutyl 2-methyl-4-heptafluoroisopropylphenyl 42 2,2-dichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 43 1,3-dichloro-2-propyl 2-methyl-4-heptafluoroisopropylphenyl 44 3-chloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 45 3,3,3-trichloro-n-propyl 2-methyl-4-heptafluoroisopropylphenyl 46 2-bromoethyl 2-methyl-4-heptafluoroisopropylphenyl 47 2,2,2-tribromoethyl 2-methyl-4-heptafluoroisopropylphenyl 48 2-iodoethyl 2-methyl-4-heptafluoroisopropylphenyl 49 tetrahydrofuran-3-yl 2-methyl-4-heptafluoroisopropylphenyl 50 (furan-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 51 (furan-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 52 (tetrahydrofuran-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 53 (tetrahydrofuran-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 54 (thiophen-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 55 (thiophen-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 56 (pyridin-2-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 57 (pyridin-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 58 (6-chloropyridin-3-yl)methyl 2-methyl-4-heptafluoroisopropylphenyl 59 Me 2,6-dimethyl-4-heptafluoroisopropylphenyl 60 Et 2,6-dimethyl-4-heptafluoroisopropylphenyl 61 n-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 62 i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 63 n-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl 64 i-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl 65 s-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl 66 t-Bu 2,6-dimethyl-4-heptafluoroisopropylphenyl 67 neopentyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 68 1,2-dimethyl-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 69 1-methyl-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 70 1,3-dimethyl-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 71 3,3-dimethyl-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 72 cyclopentylmethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 73 1-phenylethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 74 2-phenylethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 75 vinyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 76 allyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 77 propargyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 78 cyclobutyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 79 cyclopentyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 80 cyclohexyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 81 benzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 82 4-methylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 83 4-tritluoromethylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 84 3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 85 4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 86 2-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 87 3-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 88 4-fluorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 89 2-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 90 3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 91 4-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 92 4-nitrobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 93 4-methoxycarbonylbenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 94 2-hydroxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 95 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 96 2-ethoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 97 2-isopropyloxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 98 2-benzyloxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 99 3-ethoxy-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 100 ethoxycarbonylmethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 101 1-(methoxycarbonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 102 1-(ethoxycarbonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 103 3-oxo-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 104 2-acetoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 105 cyanomethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 106 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 107 3-cyano-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 108 2-(methylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 109 2-(ethylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 110 2-(isopropylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 111 1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 112 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 113 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 114 3-(methylthio)-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 115 3-(ethylthio)-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 116 2-fluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 117 2,2-difluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 118 2,2,2-trifluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 119 1,3-difluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 120 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 121 1-methyl-2,2,2-trifluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 122 1,1,1,3,3,3-hexafluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 123 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 124 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 125 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 126 4,4,4-tifluoro-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 127 2,2,3,3-tetrafluorocyclobutyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 128 chloromethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 129 trichloromethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 130 2-chloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 131 2,2-dichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 132 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 133 1,2,2,2-tetrachloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 134 1,3-dichloro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 135 1,1-dimethyl-2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 136 3-chloro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 137 2-bromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 138 2,2,2-tribromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 139 3-bromo-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 140 2-iodoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 141 2-(acetylamino)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 142 2-(dimethylamino)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 143 2-(ethylamino)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 144 methylaminocarbonylethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 145 phenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 146 4-methylphenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 147 3-trifluoromethylphenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 148 4-chlorophenyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 149 naphthyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 150 Pyridine-2-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 151 pyridine-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 152 pyridine-4-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 153 tetrahydrofuran-2-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 154 tetrahydrofuran-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 155 (furan-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 156 (furan-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 157 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 158 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 159 (thiophen-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 160 (thiophen-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 161 (pyridin-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 162 (pyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 163 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 164 Me 2-methyl-6-isopropyl-4-heptafluoro isopropylphenyl 165 Et 2-methyl-6-isopropyl-4-heptafluoro isopropylphenyl 166 i-Pr 4-heptafluoroisopropylphenyl 167 i-Pr 3-methyl-4-heptafluoroisopropylphenyl 168 i-Pr 2-ethyl-4-heptafluoroisopropylphenyl 169 i-Pr 2-propyl-4-heptafluoroisopropylphenyl 170 i-Pr 3-methoxy-4-heptafluoroisopropylphenyl 171 i-Pr 3-chloro-4-heptafluoroisopropylphenyl 172 i-Pr 2,3-dimethyl-4-heptafluoroisopropylphenyl 173 i-Pr 2,5-dimethyl-4-heptafluoroisopropylphenyl 174 i-Pr 2,6-diethyl-4-heptafluoroisopropylphenyl 175 i-Pr 2-ethyl-6-methyl-4-heptafluoroisopropylphenyl 176 i-Pr 2-methyl-6-isopropyl-4-heptafluoroisopropyl phenyl 177 i-Pr 2-methoxy-6-methyl-4-heptafluoroisopropylphenyl 178 i-Pr 2-methyl-6-phenyl4-heptafluoroisopropylphenyl 179 i-Pr 2-chloro-5-methyl-4-heptafluoroisopropylphenyl 180 i-Pr 2-chloro-6-ethyl-4-heptafluoroisopropylphenyl 181 i-Pr 2-chloro-6-n-propyl-4-heptafluoroisopropyl phenyl 182 i-Pr 2-chloro-5-methoxy-4-heptafluoroisopropylphenyl 183 i-Pr 2,3-dimethyl-6-chloro-4-heptafluoroisopropyl phenyl 184 i-Pr 2-chloro-3,6-dimethyl-4-heptafluoroisopropyl phenyl 185 i-Pr 2-methyl-3-chloromethyl-6-chloro-4-heptafluoro isopropylphenyl 186 i-Pr 2-methyl-3-iodo-6-chloro-4-heptafluoro isopropylphenyl 187 2,2,2-trichloroethyl 4-heptafluoroisopropylphenyl 188 2,2,2-trichloroethyl 3-methyl-4-heptafluoroisopropylphenyl 189 2,2,2-trichloroethyl 2-ethyl-4-heptafluoroisopropylphenyl 190 2,2,2-trichloroethyl 2-propyl-4-heptafluoroisopropylphenyl 191 2,2,2-trichloroethyl 3-methoxy-4-heptafluoroisopropylphenyl 192 2,2,2-trichloroethyl 2-chloro-4-heptafluoroisopropylphenyl 193 2,2,2-trichloroethyl 3-chloro-4-heptafluoroisopropylphenyl 194 2,2,2-trichloroethyl 2,3-dimethyl-4-heptafluoroisopropylphenyl 195 2,2,2-trichloroethyl 2,5-dimethyl-4-heptafluoroisopropylphenyl 196 2,2,2-trichloroethyl 2,6-diethyl-4-heptafluoroisopropylphenyl 197 2,2,2-trichloroethyl 2-ethyl-6-methyl-4-heptafluoroisopropylphenyl 198 2,2,2-trichloroethyl 2-methyl-6-isopropyl-4-heptafluoro isopropylphenyl 199 2,2,2-trichloroethyl 2-methoxy-6-methyl-4-heptafluoroisopropylphenyl 200 2,2,2-trichloroethyl 2-methyl-6-phenyl-4-heptafluoroisopropylphenyl 201 2,2,2-trichloroethyl 2-hydroxy-6-methyl-4-heptafluoroisopropyl phenyl 202 2,2,2-trichloroethyl 2-chloro-5-methyl-4-heptafluoroisopropylphenyl 203 2,2,2-trichloroethyl 2-methyl-3-amino-4-heptafluoroisopropylphenyl 204 2,2,2-trichloroethyl 2-methyl-3-t-butoxycarbonylamino-4-heptafluoro isopropylphenyl 205 2,2,2-trichloroethyl 2-chloro-6-ethyl-4-heptafluoroisopropylphenyl 206 2,2,2-trichloroethyl 2-bromo-6-ethyl-4-heptafluoroisopropylphenyl 207 2,2,2-trichloroethyl 2-ethyl-6-iodo-4-heptafluoroisopropylphenyl 208 2,2,2-trichloroethyl 2-chloro-6-n-propyl-4-heptafluoro isopropylphenyl 209 2,2,2-trichloroethyl 2-bromo-6-n-propyl-4-heptafluoro isopropylphenyl 210 2,2,2-trichloroethyl 2-bromo-6-n-butyl-4-heptafluoro isopropylphenyl 211 2,2,2-trichloroethyl 2-chloro-5-methoxy-4-heptafluoro isopropylphenyl 212 2,2,2-trichloroethyl 2-bromo-6-methylthio-4-heptafluoro isopropylphenyl 213 2,2,2-trichloroethyl 2,6-dichloro-4-heptafluoroisopropylphenyl 214 2,2,2-trichloroethyl 2,3-dimethyl-6-chloro-4-heptafluoro isopropylphenyl 215 2,2,2-trichloroethyl 2-chloro-3,6-dimethyl-4-heptafluoro isopropylphenyl 216 2,2,2-trichloroethyl 2-methyl-3-chloromethyl-6-chloro-4-heptafluoro isopropylphenyl 217 2,2,2-trichloroethyl 2-methyl-3,6-dichloro-4-heptafluoro isopropylphenyl 218 2,2,2-trichloroethyl 2-methyl-3-bromo-6-chloro-4-heptafluoro isopropylphenyl 219 2,2,2-trichloroethyl 2-methyl-3-iodo-6-chloro-4-heptafluoro isopropylphenyl 220 2,2,2-trichloroethyl 2-methyl-3-amino-6-chloro-4-heptafluoro isopropylphenyl 221 3,3,3-trifluoro-n-propyl 2-bromo-6-n-butyl-4-heptafluoro isopropylphenyl 222 i-Pr 2-chloro-6-methyl-4-trifluoromethylphenyl 223 i-Pr 2,6-dichloro-4-trifluoromethylphenyl 224 i-Pr 2-bromo-4,6-bis(trifluoromethyl)phenyl 225 i-Pr 2,6-dimethyl-4-heptafluoro-n-propylphenyl 226 i-Pr 2,6-dimethyl-4-nonafluoro-n-butylphenyl 227 2,2,2-trichloroethyl 4-trifluoromethylphenyl 228 2,2,2-trichloroethyl 2-chloro-6-methyl-4-trifluoromethylphenyl 229 2,2,2-trichloroethyl 2-bromo-6-chloro-4-trifluoromethylphenyl 230 2,2,2-trichloroethyl 2,6-dichloro-4-trifluoromethylphenyl 231 2,2,2-trichloroethyl 2-chloro4,6-bistrifluoromethylphenyl 232 2,2,2-trichloroethyl 2-bromo-4,6-bistrifluoromethylphenyl 233 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoro-n-propylphenyl 234 2,2,2-trichloroethyl 2,6-dimethyl-4-nonafluoro-n-butylphenyl 235 2,2,2-trichloroethyl 2,3,5,6-tetrafluoro-4-trifluoromethylphenyl 236 2,2,2-trichloroethyl 2,6-dibromo-4-pentafluoroethylphenyl 237 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-pentafluoroethylphenyl 238 3,3,3-trifluoro-n-propyl 2-bromo6-chloro-4-trifluoromethylphenyl 239 Et 2,4-bis(trifluoromethyl)phenyl 240 i-Pr 2,4-bis(trifluoromethyl)phenyl 241 vinyl 2,4-bis(trifluoromethyl)phenyl 242 cyclopentyl 2,4-bis(trifluoromethyl)phenyl 243 2-chloroethyl 2,4-bis(trifluoromethyl)phenyl 244 2-cyanoethyl 2,4-bis(trifluoromethyl)phenyl 245 2,2-difluoroethyl 2,4-bis(trifluoromethyl)phenyl 246 2,2-dichloroethyl 2,4-bis(trifluoromethyl)phenyl 247 2,2,2-trichloroethyl 2,4-bis(trifluoromethyl)phenyl 248 2,2,2-tribromoethyl 2,4-bis(trifluoromethyl)phenyl 249 3,3,3-trifluoro-n-propyl 2,4-bis(trifluoromethyl)phenyl 250 2,2,3,3,3-pentafluoro-n-propyl 2,4-bis(trifluoromethyl)phenyl 251 4-cyanobenzyl 2,4-bis(trifluoromethyl)phenyl 252 (6-chloropyridin-3-yl)methyl 2,4-bis(trifluoromethyl)phenyl 253 i-Pr 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 254 2,2-difluoroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 255 1,3-difluoro-2-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 256 2,2,2-trifluoroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 257 2,2,2-trichloroethyl 2,6-dimethyl-4-(noanfluoro-2-butyl)phenyl 258 1-methyl-2,2,2-trifluoroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 259 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 260 Et 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 261 vinyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 262 propargyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 263 cyclobutyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 264 cyclopentyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 265 benzyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 266 3-cyanobenzyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 267 4-cyanobenzyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 268 3-chlorobenzyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 269 2-methoxyethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 270 2-cyanoethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 271 2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 272 2-(ethylthio)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 273 1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 274 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 275 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 276 2-fluoroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 277 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 278 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 279 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 280 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 281 2,2,3,3-tetrafluorocyclobutyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 282 2-chloroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 283 2,2-dichloroethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 284 1,3-dichloro-2-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 285 3-chloro-n-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 286 2-bromoethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 287 2,2,2-tribromoethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 288 3-bromo-n-propyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 289 2-iodoethyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 290 tetrahydrofuran-3-yl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 291 (furan-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 292 (furan-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 293 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 294 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 295 (thiophen-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 296 (thiophen-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 297 (pyridin-2-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 298 (pyridin-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 299 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 300 2,2,2-trichloroethyl 2,6-dichloro-4-(trifluoromethylthio)phenyl 301 2,2,2-trichloroethyl 2,6-dichloro-4-(trifluoromethylsulfonyl)phenyl 302 Et 2,6-dimethyl-4-pentafluoroethylphenyl 303 i-Pr 2,6-dimethyl-4-pentafluoroethylphenyl 304 propargyl 2,6-dimethyl-4-pentafluoroethylphenyl 305 cyclobutyl 2,6-dimethyl-4-pentafluoroethylphenyl 306 cyclopentyl 2,6-dimethyl-4-pentafluoroethylphenyl 307 benzyl 2,6-dimethyl-4-pentafluoroethylphenyl 308 3-cyanobenzyl 2,6-dimethyl-4-pentafluoroethylphenyl 309 4-cyanobenzyl 2,6-dimethyl-4-pentafluoroethylphenyl 310 3-chlorobenzyl 2,6-dimethyl-4-pentafluoroethylphenyl 311 2-methoxyethyl 2,6-dimethyl-4-pentafluoroethylphenyl 312 2-cyanoethyl 2,6-dimethyl-4-pentafluoroethylphenyl 313 2-(methylthio)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl 314 2-(ethylthio)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl 315 1-methyl2-(methylthio)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl 316 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl 317 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-pentafluoroethylphenyl 318 2-fluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 319 2,2-difluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 320 2,2,2-trifluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 321 1,3-difluoro-2-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 322 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 323 1-methyl-2,2,2-trifluoroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 324 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 325 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 326 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-pentafluoroethylphenyl 327 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-pentafluoroethylphenyl 328 2,2,3,3-tetrafluorocyclobutyl 2,6-dimethyl-4-pentafluoroethylphenyl 329 2-chloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 330 2,2-dichloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 331 2,2,2-trichloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 332 1,3-dichloro-2-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 333 3-chloro-n-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 334 2-bromoethyl 2,6-dimethyl-4-pentafluoroethylphenyl 335 2,2,2-tribromoethyl 2,6-dimethyl-4-pentafluoroethylphenyl 336 3-bromo-n-propyl 2,6-dimethyl-4-pentafluoroethylphenyl 337 2-iodoethyl 2,6-dimethyl-4-pentafluoroethylphenyl 338 tetrahydrofuran-3-yl 2,6-dimethyl-4-pentafluoroethylphenyl 339 (furan-2-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 340 (furan-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 341 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 342 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 343 (thiophen-2-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 344 (thiophen-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 345 (pyridin-2-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 346 (pyridin-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 347 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-pentafluoroethylphenyl 348 Me 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 349 Et 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 350 i-Pr 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 351 propargyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 352 cyclobutyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 353 cyclopentyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 354 3-cyanobenzyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 355 4-cyanobenzyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 356 3-chlorobenzyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 357 2-methoxyethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 358 2-cyanoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 359 2-(methylthio)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 360 2-(ethylthio)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3- hexafluoro-isopropyl)phenyl 361 1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 362 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 363 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 364 2-fluoroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 365 2,2-difluoroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 366 2,2,2-trifluoroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 367 1,3-difluoro-2-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 368 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 369 1-methyl-2,2,2-trifluoroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 370 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 371 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 372 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 373 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 374 2,2,3,3-tetrafluorocyclobutyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 375 2-chloroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 376 2,2-dichloroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 377 2,2,2-trichloroethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 378 1,3-dichloro-2-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 379 3-chloro-n-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 380 2-bromoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 381 2,2,2-tribromoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 382 3-bromo-n-propyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 383 2-iodoethyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 384 tetrahydrofuran-3-yl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 385 (furan-2-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 386 (furan-3-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 387 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 388 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 389 (thiophen-2-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 390 (thiophen-3-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropylphenyl 391 (pyridin-2-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 392 (pyridin-3-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 393 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-(2-bromo-1,1,2,3,3,3-hexafluoro- isopropyl)phenyl 394 Et 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 395 i-Pr 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 396 vinyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 397 propargyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 398 cyclobutyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 399 cyclopentyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 400 benzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 401 3-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 402 4-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 403 3-chlorobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 404 2-methoxyethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 405 2-cyanoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 406 2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 407 2-(ethylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 408 1-methyl-2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 409 2-(ethylsulfinyl)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 410 2-(ethylsulfonyl)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 411 2-fluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 412 2,2-difluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 413 2,2,2-trifluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 414 1,3-difluoro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 415 1-chloro-3-fluoro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 416 1-methyl-2,2,2-trifluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 417 3,3,3-trifluoro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 418 2,2,3,3,3-pentafluoro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 419 3,3,4,4,4-pentafluoro-2-butyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 420 4,4,4-trifluoro-n-butyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 421 2,2,3,3-tetrafluorocyclobutyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 422 2-chloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 423 2,2-dichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 424 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 425 1,3-dichloro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 426 3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 427 2-bromoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 428 2,2,2-tribromoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 429 3-bromo-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 430 2-iodoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 431 tetrahydrofuran-3-yl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 432 (furan-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 433 (furan-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 434 (tetrahydrofuran-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 435 (tetrahydrofuran-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 436 (thiophen-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 437 (thiophen-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 438 (pyridin-2-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 439 (pyridin-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 440 (6-chloropyridin-3-yl)methyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 441 Et 2,6-dibromo-4-(trifluoromethylthio)phenyl 442 i-Pr 2,6-dibromo-4-(trifluoromethylthio)phenyl 443 vinyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 444 propargyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 445 cyclobutyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 446 cyclopentyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 447 benzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 448 3-cyanobenzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 449 4-cyanobenzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 450 3-chlorobenzyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 451 2-methoxyethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 452 2-cyanoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 453 2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 454 2-(ethylthio)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 455 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 456 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 457 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 458 2-fluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 459 2,2-difluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 460 2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 461 1,3-difluoro-2-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 462 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 463 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 464 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 465 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 466 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 467 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 468 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 469 2-chloroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 470 2,2-dichloroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 471 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 472 1,3-dichloro-2-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 473 3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 474 2-bromoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 475 2,2,2-tribromoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 476 3-bromo-n-propyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 477 2-iodoethyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 478 tetrahydrofuran-3-yl 2,6-dibromo-4-(trifluoromethylthio)phenyl 479 (furan-2-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 480 (furan-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 481 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 482 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 483 (thiophen-2-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 484 (thiophen-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 485 (pyridin-2-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 486 (pyridin-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 487 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(trifluoromethylthio)phenyl 488 Et 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 489 i-Pr 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 490 vinyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 491 propargyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 492 cyclobutyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 493 cyclopentyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 494 benzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 495 3-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 496 4-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 497 3-chlorobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 498 2-methoxyethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 499 2-cyanoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 500 2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 501 2-(ethylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 502 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 503 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 504 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 505 2-fluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 506 2,2-difluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 507 2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 508 1,3-difluoro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 509 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 510 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 511 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 512 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 513 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 514 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 515 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 516 2-chloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 517 2,2-dichloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 518 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 519 1,3-dichloro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 520 3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 521 2-bromoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 522 2,2,2-tribromoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 523 3-bromo-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 524 2-iodoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 525 tetrahydrofuran-3-yl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 526 (furan-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 527 (furan-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 528 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 529 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 530 (thiophen-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 531 (thiophen-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 532 (pyridin-2-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 533 (pyridin-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 534 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 535 Et 2,6-dibromo-4-(pentafluoroethylthio)phenyl 536 i-Pr 2,6-dibromo-4-(pentafluoroethylthio)phenyl 537 vinyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 538 propargyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 539 cyclobutyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 540 cyclopentyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 541 benzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 542 3-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 543 4-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 544 3-chlorobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 545 2-methoxyethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 546 2-cyanoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 547 2-(methylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 548 2-(ethylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 549 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 550 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 551 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 552 2-fluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 553 2,2-difluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 554 2,2,2-trifluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 555 1,3-difluoro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 556 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 557 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 558 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 559 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 560 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 561 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 562 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 563 2-chloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 564 2,2-dichloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 565 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 566 1,3-dichloro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 567 3-chloro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 568 2-bromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 569 2,2,2-tribromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 570 3-bromo-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 571 2-iodoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 572 tetrahydrofuran-3-yl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 573 (furan-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 574 (furan-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 575 (tetrehydrofuran-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 576 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 577 (thiophen-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 578 (thiophen-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 579 (pyridin-2-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 580 (pyridin-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 581 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 582 Et 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 583 i-Pr 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 584 vinyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 585 propargyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 586 cyclobutyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 587 cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 588 benzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 589 3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 590 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 591 3-chlorobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 592 2-methoxyethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 593 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 594 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 595 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 596 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 597 2-(ethylsulfinyl)ethyl 2,8-dibromo-4-(heptafluoro-n-propylthio)phenyl 598 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 599 2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 600 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 601 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 602 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 603 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 604 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 605 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 606 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 607 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 608 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 609 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 610 2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 611 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 612 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 613 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 614 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 615 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 616 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 617 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 618 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 619 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 620 (furan-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 621 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 622 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 623 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 624 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 625 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 626 (pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 627 (pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 628 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 629 Et 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 630 i-Pr 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 631 vinyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 632 propargyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 633 cyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 634 cyclopentyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 635 benzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 636 3-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 637 4-cyanobenzyl 2,6-dlbromo-4-(heptafluoroisopropylthio)phenyl 638 3-chlorobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 639 2-methoxyethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 640 2-cyanoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 641 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 642 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 643 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 644 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 645 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 646 2-fluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 647 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 648 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 649 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 650 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 651 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 652 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 653 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 654 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 655 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 656 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 657 2-chloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 658 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 659 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 660 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 661 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 662 2-bromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 663 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 664 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 665 2-iodoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 666 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 667 (furan-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 668 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 669 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 670 (tetrehydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 671 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 672 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 673 (pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 674 (pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 675 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 676 Et 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 677 i-Pr 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 678 vinyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 679 propargyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 680 cyclobutyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 681 cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 682 benzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 683 3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 684 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 685 3-chlorobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 686 2-methoxyethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 687 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 688 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 689 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 690 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 691 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 692 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 693 2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 694 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 695 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 696 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 697 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 698 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 699 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 700 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 701 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 702 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 703 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 704 2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 705 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 706 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 707 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 708 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 709 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 710 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 711 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 712 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 713 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 714 (furan-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 715 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 716 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 717 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 718 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 719 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 720 (pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 721 (pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 722 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 723 Et 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 724 i-Pr 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 725 vinyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 726 propargyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 727 cyclobutyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 728 cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 729 benzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 730 3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 731 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 732 3-chlorobenzyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 733 2-methoxyethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 734 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 735 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 736 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 737 1-methyl-2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 738 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 739 2-(ethylsulfonyl)ethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 740 2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 741 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 742 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 743 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl phenyl 744 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 745 1-methyl-2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 746 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 747 2,2,3,3,3-pentafluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 748 3,3,4,4,4-pentafluoro-2-butyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 749 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 750 2,2,3,3-tetrafluorocyclobutyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 751 2-chloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 752 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 753 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 754 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 755 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 756 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 757 2,2,2-tribromoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 758 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 759 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 760 tetrahydrofuran-3-yl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 761 (furan-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 762 (furan-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 763 (tetrahydrofuran-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 764 (tetrahydrofuran-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 765 (thiophen-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 766 (thiophen-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 767 (pyridin-2-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 768 (pyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 769 (6-chloropyridin-3-yl)methyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfonyl)phenyl 770 2,2,2-trichloroethyl 2-methyl-4-(heptafluoro-n-propylthio)phenyl 771 Et 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 772 i-Pr 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 773 propargyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 774 cyclobutyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 775 cyclopentyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 776 benzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 777 3-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 778 4-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 779 3-chlorobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 780 2-methoxyethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 781 2-cyanoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 782 2-(methylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 783 2-(ethylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 784 1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 785 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 786 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 787 2-fluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 788 2,2-difluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 789 2,2,2-trifluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 790 1,3-difluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 791 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 792 1-methyl-2,2,2-trifluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 793 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 794 2,2,3,3,3-pentafluoro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 795 3,3,4,4,4-pentafluoro-2-butyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 796 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 797 2,2,3,3-tetrafluorocyclobutyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 798 2-chloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 799 2,2-dichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 800 2,2,2-trichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 801 1,3-dichloro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 802 3-chloro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 803 2-bromoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 804 2,2,2-tribromoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 805 3-bromo-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 806 2-iodoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 807 tetrahydrofuran-3-yl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 808 (furan-2-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 809 (furan-3-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 810 (tetrahydrofuran-2-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 811 (tetrahydrofuran-3-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 812 (thiophen-2-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 813 (thiophen-3-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 814 (pyridin-2-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 815 (pyridin-3-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 816 (6-chloropyridin-3-yl)methyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 817 3,3,3-trifluoro-n-propyl 2-(n-butyl)-6-chloro-4-heptafluoroisopropylphenyl 818 3,3,3-trifluoro-n-propyl 2-(n-butyl)-4-heptafluoroisopropyl-6-iodophenyl 819 3,3,3-trifluoro-n-propyl 2-bromo-6-(2-butyl)-4-heptafluoroisopropylphenyl 820 i-Pr 2-methyl-4-trifluoromethoxyphenyl 821 i-Pr 2-trifluoromethyl-4-isopropylphenyl 822 i-Pr 3,5-bistrifluoromethylphenyl 823 i-Pr 2,3,4-trifluorophenyl 824 i-Pr 2-heptafluoroisopropyl-3,5-dimethylphenyl 825 i-Pr 2,4-dichloro-6-methylphenyl 826 i-Pr 2-chloro-4,6-dimethylphenyl 827 i-Pr 2,6-dimethyl-4-chlorophenyl 828 i-Pr 2,6-dimethyl-4-bromophenyl 829 i-Pr 2,6-dimethyl-4-iodophenyl 830 i-Pr 2,6-dimethyl-4-(phenyl)phenyl 831 i-Pr 2,6-dimethyl-4-(2-methylphenyl)phenyl 832 i-Pr 2,6-dimethyl-4-(3-methylphenyl)phenyl 833 i-Pr 2,6-dimethyl-4-(4-methylphenyl)phenyl 834 i-Pr 2,6-dimethyl-4-(2-methoxyphenyl)phenyl 835 i-Pr 2,6-dimethyl-4-(3-methoxyphenyl)phenyl 836 i-Pr 2,6-dimethyl-4-(4-methoxyphenyl)phenyl 837 i-Pr 2,6-dimethyl-4-(4-ethoxyphenyl)phenyl 838 i-Pr 2,6-dimethyl-4-(4-methylthiophenyl)phenyl 839 i-Pr 2,6-dimethyl-4-(2-fluorophenyl)phenyl 840 i-Pr 2,6-dimethyl-4-(3-fluorophenyl)phenyl 841 i-Pr 2,6-dimethyl-4-(4-fluorophenyl)phenyl 842 i-Pr 2-bromo-4-isopropyl-6-methylphenyl 843 i-Pr 2-chloro-4-cyano-6-methylphenyl 844 i-Pr 2-chloro-4-trifluoromethoxy-6-methylphenyl 845 i-Pr 2-chloro-4-isopropyl-6-trifluoromethylphenyl 846 i-Pr pentafluorophenyl 847 2,2,2-trichloroethyl 4-cyclohexylphenyl 848 2,2,2-trichloroethyl 2-trifluoromethylphenyl 849 2,2,2-trichloroethyl 4-(trifluoromethylthio)phenyl 850 2,2,2-trichloroethyl 4-(trifluoromethylsulfonyl)phenyl 851 2,2,2-trichloroethyl 4-(heptafluoro-n-propylthio)phenyl 852 2,2,2-trichloroethyl 4-(heptafluoro-n-propylsulfinyl)phenyl 853 2,2,2-trichloroethyl 4-(heptafluoroisopropylthio)phenyl 854 2,2,2-trichloroethyl 2-(n-butyl)-6-chloro-4-heptafluoroisopropylphenyl 855 2,2,2-trichloroethyl 2-(n-butyl)-4-heptafluoroisopropyl-6-iodophenyl 856 2,2,2-trichloroethyl 2-bromo-6-(2-butyl)-4-heptafluoroisopropylphenyl 857 2,2,2-trichloroethyl 2-(2-butyl)-4-heptafluoroisopropylphenyl 858 2,2,2-trichloroethyl 2-methyl-4-trifluoromethoxyphenyl 859 2,2,2-trichloroethyl 2-methyl-4-(2,2,2-trifluoroethoxy)phenyl 860 2,2,2-trichloroethyl 2-methyl-4-(trifluoromethylsulfonyloxy)phenyl 861 2,2,2-trichloroethyl 2-methyl-4-chlorophenyl 862 2,2,2-trichloroethyl 2-trifluoromethyl-4-isopropylphenyl 863 2,2,2-trichloroethyl 2,5-bistrifluoromethylphenyl 864 2,2,2-trichloroethyl 3,5-bistrifluoromethylphenyl 865 2,2,2-trichloroethyl 2-trifluoromethyl-4-chlorophenyl 866 2,2,2-trichloroethyl 2-chloro-6-trifluoromethylphenyl 867 2,2,2-trichloroethyl 2-trifluoromethyl-4-iodophenyl 868 2,2,2-trichloroethyl 2-trifluoromethoxy-4-bromophenyl 869 2,2,2-trichloroethyl 2,3,4-trifluorophenyl 870 2,2,2-trichloroethyl 2-heptafluoroisopropyl-3,5-dimethylphenyl 871 2,2,2-trichloroethyl 2,5-dimethyl-4-trifluoromethane sulfonyloxyphenyl 872 2,2,2-trichloroethyl 2,6-dimethyl-4-(bis(trifluoromethyl) hydroxymethyl)phenyl 873 2,2,2-trichloroethyl 2,6-dimethyl-4-(bis(chlorodifluoromethyl) hydroxymethyl)phenyl 874 2,2,2-trichloroethyl 2,6-dimethyl-4-cyanothiophenyl 875 2,2,2-trichloroethyl 2,6-dimethyl-4-chlorophenyl 876 2,2,2-trichloroethyl 2-chloro-4,6-dimethylphenyl 877 2,2,2-trichloroethyl 2,6-dimethyl-4-bromophenyl 878 2,2,2-trichloroethyl 2,6-dimethyl-4-iodophenyl 879 2,2,2-trichloroethyl 2,6-dimethyl-4-(phenyl)phenyl 880 2,2,2-trichloroethyl 2,6-dimethyl-4-(2-methylphenyl)phenyl 881 2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methylphenyl)phenyl 882 2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methylphenyl)phenyl 883 2,2,2-trichloroethyl 2,6-dimethyl-4-(2-methoxyphenyl)phenyl 884 2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methoxyphenyl)phenyl 885 2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methoxyphenyl)phenyl 886 2,2,2-trichloroethyl 2,6-dimethyl-4-(4-ethoxyphenyl)phenyl 887 2,2,2-trichloroethyl 2,6-dimethyl-4-(4-methylthiophenyl)phenyl 888 2,2,2-trichloroethyl 2,6-dimethyl-4-(2-fluorophenyl)phenyl 889 2,2,2-trichloroethyl 2,6-dimethyl-4-(3-fluorophenyl)phenyl 890 2,2,2-trichloroethyl 2,6-dimethyl-4-(4-fluorophenyl)phenyl 891 2,2,2-trichloroethyl 2,6-dimethyl-4-(3,4-difluorophenyl)phenyl 892 2,2,2-trichloroethyl 2,6-dimethyl-4-(3-methyl-4-fluorophenyl)phenyl 893 2,2,2-trichloroethyl 2,6-dimethyl-4-(furan-3-yl)phenyl 894 2,2,2-trichloroethyl 2,6-dimethyl-4-(thiophene-2-yl)phenyl 895 2,2,2-trichloroethyl 2,6-dimethyl-4-(thiophene-3-yl)phenyl 896 2,2,2-trichloroethyl 2,4-dichloro-6-methylphenyl 897 2,2,2-trichloroethyl 2,4-dichloro-6-trifluoromethylphenyl 898 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoroisopropylthio)phenyl 899 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoroisopropyl sulfonyl)phenyl 900 2,2,2-trichloroethyl 2,6-dichloro-4-pentafluorosulfanylphenyl 901 2,2,2-trichloroethyl 2,6-dibromo-4-cyclohexylphenyl 902 2,2,2-trichloroethyl 2,4-dibromo-6-trifluoromethylphenyl 903 2,2,2-trichloroethyl 2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl 904 2,2,2-trichloroethyl 2-chloro-4-hydroxy-6-methylphenyl 905 2,2,2-trichloroethyl 2-chloro-4-trifluoromethoxy-6-methylphenyl 906 2,2,2-trichloroethyl 2-chloro-4-((2,2,2-trichloroethoxy)carbonyloxy)- 6-methylphenyl 907 2,2,2-trichloroethyl 2-chloro-4-cyano-6-methylphenyl 908 2,2,2-trichloroethyl 2-chloro-4-iodo-6-methylphenyl 909 2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-methylphenyl 910 2,2,2-trichloroethyl 2-bromo-4-hydroxy-6-methylphenyl 911 2,2,2-trichloroethyl 2-chloro-4-isopropyl-6-trifluoromethylphenyl 912 2,2,2-trichloroethyl 2-bromo-4-((2,2,2-trichloroethoxy)carbonyloxy)- 6-methylphenyl 913 2,2,2-trichloroethyl 2-chloro-4-bromo-6-trifluoromethylphenyl 914 2,2,2-trichloroethyl 2-bromo-4-isopropyl-6-trifluoromethylphenyl 915 2,2,2-trichloroethyl 2-bromo-4-chloro-6-trifluoromethylphenyl 916 2,2,2-trichloroethyl pentafluorophenyl 917 2-chloroethyl 2,6-dimethyl-4-iodophenyl 918 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro2- hydroxy-2-propyl)phenyl 919 3,3,3-trifluoro-n-propyl 2,6-dichloro-4-pentafluorosulfanylphenyl 920 i-Pr 2-methyl-4-heptafluoroisopropyl-1-naphthyl 921 i-Pr 4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 922 i-Pr 2-chloro-4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 923 i-Pr 1-methyl-3-trifluoromethylpyrazol-5-yl 924 i-Pr 1-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl 925 i-Pr 1-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl 926 i-Pr 1-methyl-3-trifluoromethyl-4-methoxy carbonylpyrazol-5-yl 927 i-Pr 2-chloro-4-methylpyridin-5-yl 928 i-Pr 2-bromo4-methyl-6-chloropyridin-3-yl 929 i-Pr 2-(1,1,1,3,3,3-hexafluoroisopropyloxy) pyridin-5-yl 930 i-Pr 2-(1,1,1,3,3,3-hexafluoroisopropyloxy)- 4-methylpyridin-5-yl 931 i-Pr 2-bromo-6-(1,1,1,3,3,3-hexafluoro- isopropyloxy)pyridin-3-yl 932 i-Pr 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro- isopropyloxy)pyridin-3-yl 933 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropyl-1-naphthyl 934 2,2,2-trichloroethyl 4-heptafluoroisopropyl-5,6,7,8- tetrahydro-1-naphthyl 935 2,2,2-trichloroethyl 2-chloro-4-heptafluoroisopropyl 5,6,7,8-tetrahydro-1-naphthyl 936 2,2,2-trichloroethyl 1-methyl-3-trifluoromethylpyrazol-5-yl 937 2,2,2-trichloroethyl 1-methyl-3-trifluoromethyl-4-chloropyrazol-5-yl 938 2,2,2-trichloroethyl 1-methyl-3-trifluoromethyl-4-bromopyrazol-5-yl 939 2,2,2-trichloroethyl 1-methyl-3-trifluoromethyl-4-methoxy carbonylpyrazol-5-yl 940 2,2,2-trichloroethyl 1-(3-chloropyridine-2-yl)-3-bromopyrazol-5-yl 941 2,2,2-trichloroethyl 1-(3-chloropyridin-2-yl)-3-bromo- 4-chloropyrazol-5-yl 942 2,2,2-trichloroethyl 2-heptafluoroisopropyl-4-methylpyridin-5-yl 943 2,2,2-trichloroethyl 2-{1,1,1,3,3,3-hexafluoro isopropyloxy}pyridin-5-yl 944 2,2,2-trichloroethyl 2-(1,1,1,3,3,3-hexafluoroisopropyloxy)- 4-methylpyridin-5-yl 945 2,2,2-trichloroethyl 2-chloro-4-methylpyridin-5-yl 946 2,2,2-trichloroethyl 3-chloro-5-trifluoromethylpyridin-2-yl 947 2,2,2-trichloroethyl 2-bromo-4-methyl-6-chloropyridin-3-yl 948 2,2,2-trichloroethyl 2-bromo-6-(1,1,1,3,3,3-hexafluoro- isopropyloxy)pyridin-3-yl 949 2,2,2-trichloroethyl 2,6-dichloro-4-(trifluoromethylsulfinyl)phenyl 950 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfinyl)phenyl 951 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl 952 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfinyl)phenyl 953 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfonyl)phenyl 954 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfonyl)phenyl 955 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propyl sulfinyl)phenyl 956 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 957 2,2,2-trichloroethyl 2-chloro-6-methyl-4-(nonafluoro-2-butyl)phenyl 958 2,2,2-trichloroethyl 2-bromo-6-methyl-4-(nonafluoro-2-butyl)phenyl 959 2,2,2-trichloroethyl 2-iodo-6-methyl-4-(nonafluoro-2-butyl)phenyl 960 2,2,2-trichloroethyl 2,6-dichloro-4-(nonafluoro-2-butyl)phenyl 961 2,2,2-trichloroethyl 2,6-dibromo-4-(nonafluoro-2-butyl)phenyl 962 2,2,2-trichloroethyl 2,6-dimethyl-4-pentafluoroethylphenyl 963 2,2,2-trichloroethyl 2,6-dichloro-4-pentafluoroethylphenyl 964 2,2,2-trichloroethyl 2,6-dimethyl-4-(pentafluoroethylthio) phenyl 965 2,2,2-trichloroethyl 2,6-dimethyl-4-(pentafluoroethylsulfinyl) phenyl 966 2,2,2-trichloroethyl 2,6-dimethyl-4-(pentafluoroethylsulfonyl) phenyl 967 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylthio) phenyl 968 i-Pr 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 969 cyclobutyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 970 cyclopentyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 971 4-cyanobenzyl 2-chloro4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 972 2-methoxyethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 973 2-cyanoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 974 2-(methylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 975 2-(ethylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 976 1-methyl-2-(methylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 977 2-(ethylsulfinyl)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 978 2-(ethylsulfonyl)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 979 2-fluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 980 2,2-difluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 981 2,2,2-trifluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 982 1,3-difluoro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 983 1-chloro-3-fluoro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 984 1-methyl-2,2,2-trifluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 985 3,3,3-trifluoro-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 986 2,2,3,3,3-pentafluoro-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 987 3,3,4,4,4-pentafluoro-2-butyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 988 4,4,4-trifluoro-n-butyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 989 2,2,3,3-tetrafluorocyclobutyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 990 2-chloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 991 2,2-dichloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 992 2,2,2-trichloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 993 1,3-dichloro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 994 3-chloro-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 995 2-bromoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 996 2,2,2-tribromoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 997 3-bromo-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 998 2-iodoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 999 tetrahydrofuran-3-yl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1000 (furan-2-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1001 (furan-3-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1002 (tetrahydrofuran-2-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1003 (tetrahydrofuran-3-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1004 (thiophen-2-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1005 (thiophen-3-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1006 (pyridin-2-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1007 (pyridin-3-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1008 (6-chloropyridin-3-yl)methyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1009 Et 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1010 i-Pr 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1011 vinyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1012 propargyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1013 cyclobutyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1014 cyclopentyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1015 benzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1016 3-cyanobenzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1017 4-cyanobenzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1018 3-chlorobenzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1019 2-methoxyethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1020 2-cyanoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1021 2-(methylthio)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1022 2-(ethylthio)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1023 1-methyl-2-(methylthio)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1024 2-(ethylsulfinyl)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1025 2-(ethylsulfonyl)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1026 2-fluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1027 2,2-difluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1028 2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1029 1,3-difluoro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1030 1-chloro-3-fluoro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1031 1-methyl-2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1032 3,3,3-trifluoro-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1033 2,2,3,3,3-pentafluoro-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1034 3,3,4,4,4-pentafluoro-2-butyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1035 4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1036 2,2,3,3-tetrafluorocyclobutyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1037 2-chloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1038 2,2-dichloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1039 2,2,2-trichloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1040 1,3-dichloro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1041 3-chloro-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1042 2-bromoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1043 2,2,2-tribromoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1044 3-bromo-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1045 2-iodoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1046 tetrahydrofuran-3-yl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1047 (furan-2-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1048 (furan-3-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1049 (tetrahydrofuran-2-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1050 (tetrahydrofuran-3-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1051 (thiophen-2-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1052 (thiophen-3-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1053 (pyridin-2-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1054 (pyridin-3-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1055 (6-chloropyridin-3-yl)methyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1056 Et 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1057 i-Pr 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1058 vinyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1059 propargyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1060 cyclobutyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1061 cyclopentyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1062 benzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1063 3-cyanobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1064 4-cyanobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1065 3-chlorobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1066 2-methoxyethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1067 2-cyanoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1068 2-(methylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1069 2-(ethylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1070 1-methyl-2-(methylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1071 2-(ethylsulfinyl)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1072 2-(ethylsulfonyl)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1073 2-fluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1074 2,2-difluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1075 2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1076 1,3-difluoro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1077 1-chloro-3-fluoro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1078 1-methyl-2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1079 3,3,3-trifluoro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1080 2,2,3,3,3-pentafluoro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1081 3,3,4,4,4-pentafluoro-2-butyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1082 4,4,4-trifluoro-n-butyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1083 2,2,3,3-tetrafluorocyclobutyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1084 2-chloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1085 2,2-dichloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1086 2,2,2-trichloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1087 1,3-dichloro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1088 3-chloro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1089 2-bromoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1090 2,2,2-tribromoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1091 3-bromo-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1092 2-iodoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1093 tetrahydrofuran-3-yl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1094 (furan-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1095 (furan-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1096 (tetrahydrofuran-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1097 (tetrahydrofuran-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1098 (thiophen-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1099 (thiophen-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1100 (pyridin-2-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1101 (pyridin-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1102 (6-chloropyridin-3-yl)methyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1103 Et 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1104 i-Pr 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1105 vinyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1106 propargyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1107 cyclobutyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1108 cyclopentyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1109 benzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1110 3-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1111 4-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1112 3-chlorobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1113 2-methoxyethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1114 2-cyanoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1115 2-(methylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1116 2-(ethylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1117 1-methyl-2-(methylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1118 2-(ethylsulfinyl)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1119 2-(ethylsulfonyl)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1120 2-fluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1121 2,2-difluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1122 2,2,2-trifluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1123 1,3-difluoro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1124 1-chloro-3-fluoro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1125 1-methyl-2,2,2-trifluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1126 3,3,3-trifluoro-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1127 2,2,3,3,3-pentafluoro-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1128 3,3,4,4,4-pentafluoro-2-butyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1129 4,4,4-trifluoro-n-butyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1130 2,2,3,3-tetrafluorocyclobutyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1131 2-chloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1132 2,2-dichloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1133 2,2,2-trichloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1134 1,3-dichloro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1135 3-chloron-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1136 2-bromoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1137 2,2,2-tribromoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1138 3-bromo-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1139 2-iodoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1140 tetrahydrofuran-3-yl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1141 (furan-2-1)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1142 (furan-3-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1143 (tetrahydrofuran-2-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1144 (tetrahydrofuran-3-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1145 (thiophen-2-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1146 (thiophen-3-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1147 (pyridin-2-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1148 (pyridin-3-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1149 (6-chloropyridin-3-yl)methyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1150 Et 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1151 i-Pr 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1152 vinyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1153 propargyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1154 cyclobutyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1155 cyclopentyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1156 benzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1157 3-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1158 4-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1159 3-chlorobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1160 2-methoxyethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1161 2-cyanoethyl 2-bromo-4-methyl6-(heptafluoro isopropyl)pyridin-3-yl 1162 2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1163 2-(ethylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1164 1-methyl-2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1165 2-(ethylsulfinyl)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1166 2-(ethylsulfonyl)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1167 2-fluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1168 2,2-difluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1169 2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1170 1,3-difluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1171 1-chloro-3-fluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1172 1-methyl-2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1173 3,3,3-trifluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1174 2,2,3,3,3-pentafluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1175 3,3,4,4,4-pentafluoro-2-butyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1176 4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1177 2,2,3,3-tetrafluorocyclobutyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1178 2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1179 2,2-dichloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1180 2,2,2-trichloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1181 1,3-dichloro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1182 3-chloro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1183 2-bromoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1184 2,2,2-tribromoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1185 3-bromo-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1186 2-iodoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1187 tetrahydrofuran-3-yl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1188 (furan-2-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1189 (furan-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1190 (tetrahydrofuran-2-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1191 (tetrahydrofuran-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1192 (thiophen-2-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1193 (thiophen-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1194 (pyridin-2-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1195 (pyridin-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1196 (6-chloropyridin-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1197 Et 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1198 i-Pr 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1199 vinyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1200 propargyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1201 cyclobutyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1202 cyclopentyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1203 benzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1204 3-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1205 4-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1206 3-chlorobenzyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1207 2-methoxyethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1208 2-cyanoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1209 2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1210 2-(ethylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1211 1-methyl-2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1212 2-(ethylsulfinyl)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1213 2-(ethylsulfonyl)ethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1214 2-fluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1215 2,2-difluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1216 2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1217 1,3-difluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1218 1-chloro3-fluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1219 1-methyl-2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1220 3,3,3-trifluoro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1221 2,2,3,3,3-pentafluoro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1222 3,3,4,4,4-pentafluoro-2-butyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1223 4,4,4-trifluoro-n-butyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1224 2,2,3,3-tetrafluorocyclobutyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1225 2-chloroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1226 2,2-dichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1227 2,2,2-trichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1228 1,3-dichloro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1229 3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1230 2-bromoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1231 2,2,2-tribromoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1232 3-bromo-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1233 2-iodoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1234 tetrahydrofuran-3-yl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1235 (furan-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1236 (furan-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1237 (tetrahydrofuran-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1238 (tetrahydrofuran-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1239 (thiophen-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1240 (thiophen-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1241 (pyridin-2-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1242 (pyridin-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1243 (6-chloropyridin-3-yl)methyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1244 Et 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1245 i-Pr 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1246 vinyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1247 propargyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1248 cyclobutyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1249 cyclopentyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1250 benzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1251 3-cyanobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1252 4-cyanobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1253 3-chlorobenzyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1254 2-methoxyethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1255 2-cyanoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1256 2-(methylthio)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1257 2-(ethylthio)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1258 1-methyl-2-(methylthio)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1259 2-(ethylsulfinyl)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1260 2-(ethylsulfonyl)ethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1261 2-fluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1262 2,2-difluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1263 2,2,2-trifluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1264 1,3-difluoro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1265 1-chloro-3-fluoro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1266 1-methyl-2,2,2-trifluoroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1267 3,3,3-trifluoro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1268 2,2,3,3,3-pentafluoro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1269 3,3,4,4,4-pentafluoro-2-butyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1270 4,4,4-trifluoro-n-butyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1271 2,2,3,3-tetrafluorocyclobutyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1272 2-chloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1273 2,2-dichloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1274 2,2,2-trichloroethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1275 1,3-dichloro-2-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1276 3-chloro-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1277 2-bromoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1278 2,2,2-tribromoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1279 3-bromo-n-propyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1280 2-iodoethyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1281 tetrahydrofuran-3-yl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1282 (furan-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1283 (furan-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1284 (tetrahydrofuran-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1285 (tetrahydrofuran-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1286 (thiophen-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1287 (thiophen-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1288 (pyridin-2-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1289 (pyridin-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1290 (6-chloropyridin-3-yl)methyl 2-bromo-6-methyl-4-heptafluoroisopropylphenyl 1291 Et 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1292 i-Pr 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1293 vinyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1294 propargyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1295 cyclobutyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1296 cyclopentyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1297 benzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1298 3-cyanobenzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1299 4-cyanobenzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1300 3-chlorobenzyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1301 2-methoxyethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1302 2-cyanoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1303 2-(methylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1304 2-(ethylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1305 1-methyl-2-(methylthio)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1306 2-(ethylsulfinyl)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1307 2-(ethylsulfonyl)ethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1308 2-fluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1309 2,2-difluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1310 2,2,2-trifluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1311 1,3-difluoro-2-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1312 1-chloro-3-fluoro-2-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1313 1-methyl-2,2,2-trifluoroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1314 3,3,3-trifluoro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1315 2,2,3,3,3-pentafluoro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1316 3,3,4,4,4-pentafluoro-2-butyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1317 4,4,4-trifluoro-n-butyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1318 2,2,3,3-tetrafluorocyclobutyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1319 2-chloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1320 2,2-dichloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1321 2,2,2-trichloroethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1322 1,3-dichloro-2-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1323 3-chloro-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1324 2-bromoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1325 2,2,2-tribromoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1326 3-bromo-n-propyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1327 2-iodoethyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1328 tetrahydrofuran-3-yl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1329 (furan-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1330 (furan-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1331 (tetrahydrofuran-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1332 (tetrahydrofuran-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1333 (thiophen-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1334 (thiophen-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1335 (pyridin-2-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1336 (pyridin-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1337 (6-chloropyridin-3-yl)methyl 2-iodo-6-methyl-4-heptafluoroisopropylphenyl 1338 Et 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1339 i-Pr 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1340 vinyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1341 propargyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1342 cyclobutyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1343 cyclopentyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1344 benzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1345 3-cyanobenzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1346 4-cyanobenzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1347 3-chlorobenzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1348 2-methoxyethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1349 2-cyanoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1350 2-(methylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1351 2-(ethylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1352 1-methyl-2-(methylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1353 2-(ethylsulfinyl)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1354 2-(ethylsulfonyl)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1355 2-fluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1356 2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1357 2,2,2-trifluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1358 1,3-difluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1359 1-chloro3-fluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1360 1-methyl-2,2,2-trifluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1361 3,3,3-trifluoro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1362 2,2,3,3,3-pentafluoro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1363 3,3,4,4,4-pentafluoro-2-butyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1364 4,4,4-trifluoro-n-butyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1365 2,2,3,3-tetrafluorocyclobutyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1366 2-chloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1367 2,2-dichloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1368 2,2,2-trichloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1369 1,3-dichloro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1370 3-chloro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1371 2-bromoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1372 2,2,2-tribromoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1373 3-bromo-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1374 2-iodoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1375 tetrahydrofuran-3-yl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1376 (furan-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1377 (furan-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1378 (tetrahydrofuran-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1379 (tetrahydrofuran-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1380 (thiophen-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1361 (thiophen-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1382 (pyridin-2-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1383 (pyridin-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1384 (6-chloropyridin-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl

TABLE 2 (1-B)

Compound No. X₁ X₂ X₃ X₄ R₁ Q 1385 Me H H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropyl phenyl 1386 Me H H H i-Pr 2,6-dimethy-4-heptafluoroisopropyl phenyl 1387 Me H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1388 F H H H Et 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1389 F H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1390 F H H H vinyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1391 F H H H propargyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1392 F H H H cyclobutyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1393 F H H H cyclopentyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1394 F H H H benzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1395 F H H H 3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1396 F H H H 4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1397 F H H H 3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1398 F H H H 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1399 F H H H 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1400 F H H H 2-(methylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1401 F H H H 2-(ethylthi)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1402 F H H H 1-methyl-2-(methylthio)- 2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl 1403 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1404 F H H H 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1405 F H H H 2-fluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1406 F H H H 2,2-difluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1407 F H H H 2,2,2-trifluoroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1408 F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1409 F H H H 1-chloro-3-fluoro-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl propyl 1410 F H H H 1-methyl-2,2,2-trifluoro 2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl 1411 F H H H 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1412 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-heptafluoroisopropylphenyl propyl 1413 F H H H 3,3,4,4,4-pentafluoro-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl butyl 1414 F H H H 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1415 F H H H 2,2,3,3-tetrafluoro 2,6-dimethyl-4-heptafluoroisopropylphenyl cyclobutyl 1416 F H H H 2-chloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1417 F H H H 2,2-dichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1418 F H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1419 F H H H 1,3-dichloro-2-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1420 F H H H 3-chloro-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1421 F H H H 2-bromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1422 F H H H 2,2,2-tribromoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1423 F H H H 3-bromo-n-propyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1424 F H H H 2-idoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1425 F H H H tetrahydrofuran-3-yl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1426 F H H H (furan-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1427 F H H H (furan-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1428 F H H H (tetrahydrofuran-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl yl)methyl 1429 F H H H (tetrahydrofuran-3- 2,6-dimethyl-4-heptafluoroisopropylphenyl yl)methyl 1430 F H H H (thiophen-2-yl)methyl 2,6-dimethyl-4-heprafluoroisopropylphenyl 1431 F H H H (thiophen-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1432 F H H H (pyridin-2-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1433 F H H H (pyridin-3-yl)methyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1434 F H H H (6-chloropyridin-3- 2,6-dimethyl-4-heptafluoroisopropylphenyl yl)methyl 1435 F H H H Et 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1436 F H H H i-Pr 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1437 F H H H vinyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1438 F H H H propargyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1439 F H H H cyclobutyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1440 F H H H cyclopentyl 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 1441 F H H H benzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1442 F H H H 3-cyanobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1443 F H H H 4-cyanobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1444 F H H H 3-chlorobenzyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1445 F H H H 2-methoxyethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1446 F H H H 2-cyanoethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1447 F H H H 2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1448 F H H H 2-(ethylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1449 F H H H 1-methyl-2-(methylthio)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1450 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1451 F H H H 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1452 F H H H 2-fluoroethyl 2,6-dimethyl-4-(nonefluoro2-butyl) phenyl 1453 F H H H 2,2-difluoroethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1454 F H H H 2,2,2-trifluoroethyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1455 F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1456 F H H H 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1457 F H H H 1-methyl-2,2,2-trifluoro 2,6-dimethyl-4-(nonafluoro2-butyl) ethyl phenyl 1458 F H H H 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(nonafluoro2-butyl) phenyl 1459 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-(nonafluoro2-butyl) propyl phenyl 1460 F H H H 3,3,4,4,4-pentafluoro-2- 2,6-dimethyl-4-(nonafluoro2-butyl) butyl phenyl 1385 Me H H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1386 Me H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1387 Me H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1388 F H H H Et 2,6-dimethyl-4-heptafluoroisopropylphenyl 1389 F H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1390 F H H H vinyl 2,6-dimethyl-4-hepsafluoroisopropylphenyl 1391 F H H H propargyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1392 F H H H cyclobutyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1393 F H H H cyclopentyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1394 F H H H benzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1395 F H H H 3-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1396 F H H H 4-cyanobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1397 F H H H 3-chlorobenzyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1398 F H H H 2-methoxyethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1399 F H H H 2-cyanoethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1400 F H H H 2-(methylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1401 F H H H 2-(ethylthio)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1402 F H H H 1-methyl-2- 2,6-dimethyl-4-heptafluoroisopropylphenyl (methylthio)ethyl 1403 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1404 F H H H 2-(ethylsulfonyl)ethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1481 F H H H (6-chloropyridin-3-yl) 2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl methyl 1482 F H H H Et 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1483 F H H H i-Pr 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1484 F H H H vinyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1485 F H H H cyclobutyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1486 F H H H cyclopentyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1487 F H H H 3-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1488 F H H H 4-cyanobenzyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1489 F H H H 2-cyanoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1490 F H H H 2-(methylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1491 F H H H 2-(ethylthio)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1492 F H H H 1-methyl-2-(methylthio) 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl ethyl 1493 F H H H 2-(ethylsulfinyl)ethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1494 F H H H 2-fluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1495 F H H H 2,2-difluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1496 F H H H 2,2,2-trifluoroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1497 F H H H 1,3-difluoro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1498 F H H H 1-chloro-3-fluoro-2- 2,6-dichloro-4-(heptefluoro-n-propylthio)phenyl propyl 1499 F H H H 1-methyl-2,2,2- 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl trifluoroethyl 1500 F H H H 3,3,3-trifluoro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1501 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl propyl 1502 F H H H 4,4,4-trifluoro-n-butyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1503 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl butyl 1504 F H H H 2-chloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1505 F H H H 2,2-dichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1506 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1507 F H H H 1,3-dichloro-2-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1508 F H H H 3-chloro-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1509 F H H H 2-bromoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1510 F H H H 3-bromo-n-propyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1511 F H H H 2-iodoethyl 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl 1512 F H H H (6-chloropyridin-3-yl) 2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl methyl 1513 F H H H Et 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1514 F H H H i-Pr 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1515 F H H H vinyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1516 F H H H cyclobutyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1517 F H H H cyclopentyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1518 F H H H 3-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1519 F H H H 4-cyanobenzyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1520 F H H H 2-cyanoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1521 F H H H 2-(methylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1522 F H H H 2-(ethylthio)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1523 F H H H 1-methyl-2-(methythio) 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl ethyl 1524 F H H H 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1525 F H H H 2-fluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1526 F H H H 2,2-difluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1527 F H H H 2,2,2-trifluoroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1528 F H H H 1,3-difluoro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1529 F H H H 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1530 F H H H 2-methyl-2,2,2-trifluoro 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl ethyl 1531 F H H H 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1532 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl propyl 1533 F H H H 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1534 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl butyl 1535 F H H H 2-chloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1536 F H H H 2,2-dichloroethyl 2,6-dibromo-4-(trif1uoromethylsulfonyl)phenyl 1537 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1538 F H H H 1,3-dichloro-2-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1539 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1540 F H H H 2-bromoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1541 F H H H 3-bromo-n-propyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1542 F H H H 2-iodoethyl 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl 1543 F H H H (6-chloropyridin-3- 2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl yl)methyl 1544 F H H H Et 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1545 F H H H i-Pr 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1546 F H H H vinyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1547 F H H H cyclobutyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1548 F H H H cyclopentyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1549 F H H H 3-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1550 F H H H 4-cyanobenzyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1551 F H H H 2-cyanoethyl 2,6-dibromo-4-(pentafluoroerhylthio)phenyl 1552 F H H H 2-(methylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1553 F H H H 2-(ethylthio)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1554 F H H H 1-methyl-2- 2,6-dibromo-4-(pentafluoroethylthio)phenyl (methylthio)ethyl 1555 F H H H 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1556 F H H H 2-fluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1557 F H H H 2,2-difluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1558 F H H H 2,2,2-trifluoroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1559 F H H H 1,3-difluoro2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1560 F H H H 1-chloro-3-fluoro-2- 2,6-dibromo-4-(pentafluoroethylthio)phenyl propyl 1561 F H H H 1-methyl-2,2,2-trifluoro 2,6-dibromo-4-(pentafluoroethylthio)phenyl ethyl 1562 F H H H 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1563 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(pentafluoroethylthio)phenyl propyl 1564 F H H H 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1565 F H H H 2,2,3,3-tetrafluoro 2,6-dibromo-4-(pentafluoroethylthio)phenyl cyclobutyl 1566 F H H H 2-chloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1567 F H H H 2,2-dichloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1568 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1569 F H H H 1,3-dichloro-2-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1570 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1571 F H H H 2-bromoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1572 F H H H 3-bromo-n-propyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1573 F H H H 2-iodoethyl 2,6-dibromo-4-(pentafluoroethylthio)phenyl 1574 F H H H (6-chloropyridin-3-yl) 2,6-dibromo-4-(pentafluoroethylthio)phenyl methyl 1575 F H H H Et 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1576 F H H H i-Pr 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1577 F H H H vinyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1578 F H H H cyclobutyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1579 F H H H cyclopentyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1580 F H H H 3-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1581 F H H H 4-cyanobenzyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1582 F H H H 2-cyanoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1583 F H H H 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1584 F H H H 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1585 F H H H 1-methyl-2-(methylthio) 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl ethyl 1586 F H H H 2-(ethylsulfinyl)ethyl 2,6-dlbromo-4-(heptafluoro-n-propylthio)phenyl 1587 F H H H 2-fluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1588 F H H H 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1589 F H H H 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1590 F H H H 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1591 F H H H 1-chloro-3-fluoro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1592 F H H H 1-methyl-2,2,2-trifluoro 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl ethyl 1593 F H H H 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1594 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl propyl 1595 F H H H 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1596 F H H H 2,2,3,3-tetrafluoro 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl cyclobutyl 1597 F H H H 2-chlooroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1598 F H H H 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1599 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1600 F H H H 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1601 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1602 F H H H 2-bromoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1603 F H H H 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1604 F H H H 2-iodoethyl 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 1605 F H H H (6-chloropyridin-3-yl) 2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl methyl 1606 F H H H Et 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1607 F H H H i-Pr 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1608 F H H H vinyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1609 F H H H cyclobutyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1610 F H H H cyclopentyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1611 F H H H 3-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1612 F H H H 4-cyanobenzyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1613 F H H H 2-cyanoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1614 F H H H 2-(methylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1615 F H H H 2-(ethylthio)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1616 F H H H 1-methyl-2-(methylthio) 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl ethyl 1617 F H H H 2-(ethylsulfinyl)ethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1618 F H H H 2-fluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1619 F H H H 2,2-difluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1620 F H H H 2,2,2-trifluoroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1621 F H H H 1,3-difluoro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1622 F H H H 1-chloro-3-fluoro2-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1623 F H H H 1-methyl-2,2,2-trifluoro 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl ethyl 1624 F H H H 3,3,3-trifluoro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1625 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl propyl 1626 F H H H 4,4,4-trifluoro-n-butyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1627 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl butyl 1628 F H H H 2-chloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1629 F H H H 2,2-dichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1630 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1631 F H H H 1,3-dichloro-2-propyl 2,6-dibromo-4-(heptafluoroisopropylshio)phenyl 1632 F H H H 3-chloro-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1633 F H H H 2-bromoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1634 F H H H 3-bromo-n-propyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1635 F H H H 2-iodoethyl 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl 1636 F H H H (6-chloropyridin-3-yl) 2,6-dibromo-4-(heptafluoroisopropylthio)phenyl methyl 1637 F H H H Et 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1638 F H H H i-Pr 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1639 F H H H vinyl 2,6-dimethyl-4-(heptefluoro-n-propylthio)phenyl 1640 F H H H cyclobutyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1641 F H H H cyclopentyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1642 F H H H 3-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1643 F H H H 4-cyanobenzyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1644 F H H H 2-cyanoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1645 F H H H 2-(methylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1646 F H H H 2-(ethylthio)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1647 F H H H 1-methyl-2-(methylthio) 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl ethyl 1648 F H H H 2-(ethylsulfinyl)ethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1649 F H H H 2-fluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1650 F H H H 2,2-difluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1651 F H H H 2,2,2-trifluoroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1652 F H H H 1,3-difluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1653 F H H H 1-chloro-3-fluoro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1654 F H H H 1-methyl-2,2,2-trifluoro 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl ethyl 1655 F H H H 3,3,3-trifluoro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1656 F H H H 2,2,3,3,3-pentafluoro-n- 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl propyl 1657 F H H H 4,4,4-trifluoro-n-butyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1658 F H H H 2,2,3,3-tetrafluorocyclo 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl butyl 1659 F H H H 2-chloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1660 F H H H 2,2-dichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1661 F H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1662 F H H H 1,3-dichloro-2-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1663 F H H H 3-chloro-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1664 F H H H 2-bromoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1665 F H H H 3-bromo-n-propyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1666 F H H H 2-iodoethyl 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl 1667 F H H H (6-chloropyridin-3- 2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl yl)methyl 1668 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(trifluoromethylsulfinyl)phenyl 1669 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(trifluoromethylsulfinyl)phenyl 1670 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfinyl)phenyl 1671 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfinyl)phenyl 1672 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(pentafluoroethylsulfonyl)phenyl 1673 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(pentafluoroethylsulfonyl)phenyl 1674 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(heptafluoro-n-propyl sulfinyl)phenyl 1675 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(heptafluoro-n-propyl sulfinyl)phenyl 1676 F H H H 2,2,2-trichloroethyl 2-chloro-6-methyl-4-(nonafluoro-2-butyl)phenyl 1677 F H H H 2,2,2-trichloroethyl 2-bromo-6-methyl-4-(nonafluoro-2-butyl)phenyl 1678 F H H H 2,2,2-trichloroethyl 2-iodo-6-methyl-4-(nonafluoro-2-butyl)phenyl 1679 F H H H 2,2,2-trichloroethyl 2,6-dichloro-4-(nonafluoro-2-butyl)phenyl 1680 F H H H 2,2,2-trichloroethyl 2,6-dibromo-4-(nonafluoro-2-butyl)phenyl 1681 F H H H Et 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1682 F H H H i-Pr 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1683 F H H H vinyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1684 F H H H cyclobutyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1685 F H H H clopentyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1686 F H H H 3-cyanobenzyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1687 F H H H 4-cyanobenzyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1688 F H H H 2-cyanoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1689 F H H H 2-(methylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1690 F H H H 2-(ethylthio)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1691 F H H H 1-methyl-2-(methylthio) 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1692 F H H H 2-(ethylsulfinyl)ethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1693 F H H H 2-fluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1694 F H H H 2,2-difluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1695 F H H H 2,2,2-trifluoroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1696 F H H H 1,3-difluoro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1697 F H H H 1-chloro-3-fluoro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1698 F H H H 1-methyl-2,2,2-trifluoro 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1699 F H H H 3,3,3-trifluoro-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1700 F H H H 2,2,3,3,3-pentafluoro-n- 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl isopropyloxy)pyridin-3-yl 1701 F H H H 4,4,4-trifluoro-n-butyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1702 F H H H 2,2,3,3-tetrafluoro 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl isopropyloxy)pyridin-3-yl 1703 F H H H 2-chloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1704 F H H H 2,2-dichloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1705 F H H H 2,2,2-trichloroethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridln-3-yl 1706 F H H H 1,3-dichloro-2-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1707 F H H H 3-chloro-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1708 F H H H 2-bromoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1709 F H H H 3-bromo-n-propyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1710 F H H H 2-iodoethyl 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1711 F H H H (6-chloropyridin-3-yl) 2-chloro-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl isopropyloxy)pyridin-3-yl 1712 F H H H Et 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1713 F H H H i-Pr 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1714 F H H H vinyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1715 F H H H cyclobutyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1716 F H H H cyclopentyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1717 F H H H 3-cyanobenzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1718 F H H H 4-cyanobenzyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1719 F H H H 2-cyanoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1720 F H H H 2-(methylthio)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1721 F H H H 2-(ethylthio)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1722 F H H H 1-methyl-2-(methylthio) 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1723 F H H H 2-(ethylsulfinyl)ethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1724 F H H H 2-fluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1725 F H H H 2,2-difluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1726 F H H H 2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1727 F H H H 1,3-difluoro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1728 F H H H 1-chloro-3-fluoro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1729 F H H H 1-methyl-2,2,2-trifluoro 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1730 F H H H 3,3,3-trifluoro-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1731 F H H H 2,2,3,3,3-pentafluoro-n- 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl isopropyloxy)pyridin-3-yl 1732 F H H H 4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1733 F H H H 2,2,3,3-tetrafluoro 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl isopropyloxy)pyridin-3-yl 1734 F H H H 2-chloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1735 F H H H 2,2-dichloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1736 F H H H 2,2,2-trichloroethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1737 F H H H 1,3-dichloro-2-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1738 F H H H 3-chloro-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1739 F H H H 2-bromoethyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1740 F H H H 3-bromo-n-propyl 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1741 F H H H 2-iodoethyl 2-bromo-4-methyl-6-(2,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1742 F H H H (6-chloropyridin-3-yl) 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl isopropyloxy)pyridin-3-yl 1743 F H H H Et 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1744 F H H H i-Pr 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1745 F H H H vinyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1746 F H H H cyclobutyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1747 F H H H cyclopentyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1748 F H H H 3-cyanobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy(pyridin-3-yl 1749 F H H H 4-cyanobenzyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1750 F H H H 2-cyanoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1751 F H H H 2-(methylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1752 F H H H 2-(ethylthio)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1753 F H H H 1-methyl-2-(methylthio) 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1754 F H H H 2-(ethylsulfinyl)ethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1755 F H H H 2-fluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1756 F H H H 2,2-difluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1757 F H H H 2,2,2-trifluoroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1758 F H H H 1,3-difluoro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1759 F H H H 1-chloro-3-fluoro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1760 F H H H 1-methyl-2,2,2-trifluoro 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1761 F H H H 3,3,3-trifluoro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1762 F H H H 2,2,3,3,3-pentafluoro-n- 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro propyl isopropyloxy)pyridin-3-yl 1763 F H H H 4,4,4-trifluoro-n-butyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexefluoro isopropyloxy)pyridin-3-yl 1764 F H H H 2,2,3,3-tetrafluoro 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl isopropyloxy)pyridin-3-yl 1765 F H H H 2-chloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1766 F H H H 2,2-dichloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1767 F H H H 2,2,2-trichloroethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1768 F H H H 1,3-dichloro-2-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1769 F H H H 3-chloro-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1770 F H H H 2-bromoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1771 F H H H 3-bromo-n-propyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyioxy)pyridin-3-yl 1772 F H H H 2-iodoethyl 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1773 F H H H (6-chloropyridin-3-yl) 2-iodo-4-methyl-6-(1,1,1,3,3,3-hexafluoro methyl isopropyloxy)pyridin-3-yl 1774 F H H H Et 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1775 F H H H i-Pr 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyioxy)pyridin-3-yl 1776 F H H H vinyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1777 F H H H cyclobutyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1778 F H H H cyclopentyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1779 F H H H 3-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1780 F H H H 4-cyanobenzyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1781 F H H H 2-cyanoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1782 F H H H 2-(methylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1783 F H H H 2-(ethylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1784 F H H H 1-methyl-2-(methylthio)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1785 F H H H 2-(ethylsulfinyl)ethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1786 F H H H 2-fluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1787 F H H H 2,2-difluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1788 F H H H 2,2,2-trifluoroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1789 F H H H 1,3-difluoro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1790 F H H H 1-chloro-3-fluoro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1791 F H H H 1-methyl-2,2,2-trifluoro 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro ethyl isopropyloxy)pyridin-3-yl 1792 F H H H 3,3,3-trifluoro-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1793 F H H H 2,2,3,3,3-pentafluoro-n- 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro propyl isopropyloxy)pyridin-3-yl 1794 F H H H 4,4,4-trifluoro-n-butyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1795 F H H H 2,2,3,3-tetrafluoro 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro cyclobutyl isopropyloxy)pyridin-3-yl 1796 F H H H 2-chloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1797 F H H H 2,2-dichloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1798 F H H H 2,2,2-trichloroethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1799 F H H H 1,3-dichloro-2-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1800 F H H H 3-chloro-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1801 F H H H 2-bromoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1802 F H H H 3-bromo-n-propyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1803 F H H H 2-iodoethyl 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro isopropyloxy)pyridin-3-yl 1804 F H H H (6-chloropyridin-3-yl) 2,4-dimethyl-6-(1,1,1,3,3,3-hexafluoro methyl isopropyloxy(pyridin-3-yl 1805 F H H H Et 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1806 F H H H i-Pr 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1807 F H H H vinyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1808 F H H H cyclobutyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1809 F H H H cyclopentyl 2-bromo-4-methyl-8-(heptafluoro isopropyl)pyridin-3-yl 1810 F H H H 3-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1811 F H H H 4-cyanobenzyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1812 F H H H 2-cyanoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1813 F H H H 2-(methylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1814 F H H H 2-(ethylthio)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1815 F H H H 1-methyl-2-(methylthio) 2-bromo-4-methyl-6-(heptafluoro ethyl isopropyl)pyridin-3-yl 1816 F H H H 2-(ethylsulfinyl)ethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1817 F H H H 2-fluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1818 F H H H 2,2-difluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1819 F H H H 2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1820 F H H H 1,3-difluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1821 F H H H 1-chloro-3-fluoro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1822 F H H H 1-methyl-2,2,2-trifluoroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1823 F H H H 3,3,3-trifluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1824 F H H H 2,2,3,3,3-pentafluoro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1825 F H H H 4,4,4-trifluoro-n-butyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1826 F H H H 2,2,3,3-tetrafluorocyclobutyl 2-bromo--methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1827 F H H H 2-chloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1828 F H H H 2,2-dichloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1829 F H H H 2,2,2-trichloroethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1830 F H H H 1,3-dichloro-2-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1831 F H H H 3-chloro-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1832 F H H H 2-bromoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl(pyridin-3-yl 1833 F H H H 3-bromo-n-propyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1834 F H H H 2-iodoethyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1835 F H H H (6-chloropyridin-3-yl)methyl 2-bromo-4-methyl-6-(heptafluoro isopropyl)pyridin-3-yl 1836 F H H H Et 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1837 F H H H i-Pr 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1838 F H H H vinyl 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1839 F H H H cyclobutyl 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1840 F H H H cyclopentyl 2-chloro-6-methyl-4- heptafluoroisopropylphenyl 1841 F H H H 3-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1842 F H H H 4-cyanobenzyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1843 F H H H 2-cyanoethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1844 F H H H 2-(methylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1845 F H H H 2-(ethylthio)ethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1846 F H H H 1-methyl-2-(methylthio) 2-chloro-6-methyl-4-heptafluoroisopropyl ethyl phenyl 1847 F H H H 2-(ethylsulfinyl)ethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1848 F H H H 2-fluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1849 F H H H 2,2-difluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1850 F H H H 2,2,2-trifluoroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1851 F H H H 1,3-difluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1852 F H H H 1-chloro-3-fluoro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1853 F H H H 1-methyl-2,2,2- 2-chloro-6-methyl-4-heptafluoroisopropyl trifluoroethyl phenyl 1854 F H H H 3,3,3-trifluoro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1855 F H H H 2,2,3,3,3-pentafluoro-n- 2-chloro-6-methyl-4-heptafluoroisopropyl propyl phenyl 1856 F H H H 4,4,4-trifluoro-n-butyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1857 F H H H 2,2,3,3-tetrafluoro 2-chloro-6-methyl-4-heptafluoroisopropyl cyclobutyl phenyl 1858 F H H H 2-chloroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1859 F H H H 2,2-dichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1860 F H H H 2,2,2-trichloroethyl 2-chloro-6-methyl-4-heptafluoroisopropyl phenyl 1861 F H H H 1,3-dichloro-2-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1862 F H H H 3-chloro-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1863 F H H H 2-bromoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1864 F H H H 3-bromo-n-propyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1865 F H H H 2-iodoethyl 2-chloro-6-methyl-4-heptafluoroisopropylphenyl 1866 F H H H (6-chloropyridin-3-yl) 2-chloro-6-methyl-4-heptafluoroisopropylphenyl methyl 1867 F H H H Et 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1868 F H H H i-Pr 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1869 F H H H vinyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1870 F H H H cyclobutyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1871 F H H H cyclopentyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1872 F H H H 3-cyanobenzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1873 F H H H 4-cyanobenzyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1874 F H H H 2-cyanoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1875 F H H H 2-(methylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1876 F H H H 2(ethylthio)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1877 F H H H 1-methyl-2-(methylthio) 2-iodo-6-n-propyl-4-heptafluoro ethyl isopropylphenyl 1878 F H H H 2-(ethylsulfinyl)ethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1879 F H H H 2-fluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1880 F H H H 2,2-difluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1881 F H H H 2,2,2-trifluoroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1882 F H H H 1,3-difluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1883 F H H H 1-chloro-3-fluoro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1884 F H H H 1-methyl-2,2,2-trifluoro 2-iodo-6-n-propyl-4-heptafluoro ethyl isopropylphenyl 1885 F H H H 3,3,3-trifluoro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1886 F H H H 2,2,3,3,3-pentafluoro-n- 2-iodo-6-n-propyl-4-heptafluoro propyl isopropylphenyl 1887 F H H H 4,4,4-trifluoro-n-butyl 2-iodo-8-n-propyl-4-heptafluoro isopropylphenyl 1888 F H H H 2,2,3,3-tetrafluoro 2-iodo-6-n-propyl-4-heptafluoro cyclobutyl isopropylphenyl 1889 F H H H 2-chloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1890 F H H H 2,2-dichloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1891 F H H H 2,2,2-trichloroethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1892 F H H H 1,3-dichloro-2-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1893 F H H H 3-chloro-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1894 F H H H 2-bromoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1895 F H H H 3-bromo-n-propyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1896 F H H H 2-iodoethyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1897 F H H H (6-chloropyridin-3-yl)methyl 2-iodo-6-n-propyl-4-heptafluoro isopropylphenyl 1898 Cl H H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1899 Cl H H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1900 Cl H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1901 Cl H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1902 Cl H H H 2,2,2-trichloroethyl 2,4-bistrifluoromethylphenyl 1903 Cl H H H 2,2,2-trichloroethyl 2-(1,1,1,3,3,3-hexafluoroisopropyloxy)- 4-methylpyridin-5-yl 1904 Br H H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1905 Br H H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1906 F F H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1907 F F H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1908 F F F H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1909 H Me H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1910 H Me H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1911 H Me H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1912 H Me H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1913 H MeO H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1914 H MeO H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1915 H F H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1916 H F H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1917 H F H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1918 H F H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1919 H Cl H H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1920 H Cl H H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1921 H Cl H H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1922 H Cl H H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1923 H H Me H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1924 H H CF₃ H i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1925 H H CF₃ H 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1926 H H CF₃ H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1927 H H CF₃ H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1928 H H NH₂ H i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1929 H H Me₂N H 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1930 H H H Me i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1931 H H H Me 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1932 H H H Me i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1933 H H H Me 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1934 H H H F i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1935 H H H F 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1936 H H H F i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1937 H H H F 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1938 H H H Cl i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1939 H H H Cl 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1940 H H H Cl i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1941 H H H Cl 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl 1942 H H H Br i-Pr 2-methyl-4-heptafluoroisopropylphenyl 1943 H H H Br 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1944 H H H I 2,2,2-trichloroethyl 2-methyl-4-heptafluoroisopropylphenyl 1945 H H H I i-Pr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1946 H H H I t-Bu 2-methyl-4-heptafluoroisopropylphenyl 1947 H H H I 2,2,2-trichloroethyl 2,6-dimethyl-4-heptafluoroisopropylphenyl

TABLE 3 (1-C)

Compound No. X₁ X₂ X₃ X₄ R₁ R₂ R₃ Q 1948 H H H H 2,2,2-trichloro Me H 2,6-dibromo-4-(heptafluoro ethyl n-propylthio)phenyl 1949 H H H H 2,2,2-trichloro H Me 2-methyl-4-heptafluoroisopropyl ethyl phenyl 1950 H H H H i-Pr H Me 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1951 H H H H 2,2,2-trichloro H Me 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1952 H H H H i-Pr H Me 2-methyl-6-chloro-4- heptafluoroisopropyl phenyl 1953 H H H H 2,2,2-trichloro H Me 2-methyl-6-chloro-4- ethyl heptafluoroisopropyl phenyl 1954 H H H H i-Pr H Me 2-methyl-6-bromo-4-heptafluoroisopropyl phenyl 1955 H H H H 2,2,2-trichloro H Me 2-methyl-6-bromo-4-heptafluoroisopropyl ethyl phenyl 1956 H H H H 2,2,2-trichloro H Et 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1957 H H H H 2,2,2-trichloro H i-Pr 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1958 H H H H 2,2,2-trichloro Me H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1959 F H H H 2,2,2-trichloro Me H 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1960 H H MeNH H i-Pr Me H 2,6-dimethyl-4-heptafluoroisopropyl phenyl

TABLE 4 (1-D)

Compound No. G₁ G₂ G₃ R₁ Q 1961 O S O Me 2,6-dimethyl-4-heptafluoroisopropylphenyl 1962 O S O Et 2,6-dimethyl-4-heptafluoroisopropylphenyl 1963 O O S iPr 2,6-dimethyl-4-heptafluoroisopropylphenyl 1964 O O S 2,2,2-trichLoro 2,6-dimethyl-4-heptafluoroisopropylphenyl ethyl

TABLE 5 (1-E)

Compound No. A₁ A₂ A₃ A₄ R₁ R₂ Q 1965 N C C C i-Pr H 2-methyl-4-heptafluoroisopropylphenyl 1966 N C C C 2,2,2-trichloroethyl H 2-methyl-4-heptafluoroisopropylphenyl 1967 N C C C i-Pr H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1968 N C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1969 N C C C 2-chloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1970 N C C C 2-fluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1971 N C C C Et H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1972 N C C C vinyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1973 N C C C cyclobutyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1974 N C C C cyclopentyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1975 N C C C 3-cyanobenzyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1976 N C C C 4-cyanobeozyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1977 N C C C 2-cyanoethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1978 N C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1979 N C C C 2-(ethylthio)ethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1980 N C C C 1-methyl-2- H 2,6-dimethyl-4-heptafluoroisopropyl (methylthio)ethyl phenyl 1981 N C C C 2-(ethylsulfinyl)ethyl H 2,6-dimethyl-4-heptatluoroisopropyl phenyl 1982 N C C C 2-fluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1983 N C C C 2,2-difluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1984 N C C C 2,2,2-trifluoroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1985 N C C C 1,3-difluoro-2-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1986 N C C C 1-chloro-3-fluoro-2- H 2,6-dimethyl-4-heptafluoroisopropyl propyl phenyl 1987 N C C C 1-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-heptafluoroisopropyl ethyl phenyl 1988 N C C C 3,3,3-trifluoro-n-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1989 N C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-heptatluoroisopropyl propyl phenyl 1990 N C C C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1991 N C C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4-heptafluoroisopropyl cyclobutyl phenyl 1992 N C C C 2,2-dichloroethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1993 N C C C 1,3-dichloro-2-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1994 N C C C 3-chloro-n-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1995 N C C C 2-bromoethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1996 N C C C 3-bromo-n-propyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1997 N C C C 2-iodoethyl H 2,6-dimethyl-4-heptafluoroisopropyl phenyl 1998 N C C C (6-chloropyridin-3-yl) H 2,6-dimethyl-4-heptafluoroisopropyl methyl phenyl 1999 N C C C Et H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2000 N C C C i-Pr H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2001 N C C C vinyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2002 N C C C cyclobutyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2003 N C C C cyclopentyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2004 N C C C 3-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2005 N C C C 4-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) 2006 N C C C 2-cyanoethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2007 N C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2008 N C C C 2-(ethylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2009 N C C C 1-methyl-2-(methylthio) H 2,6-dimethyl-4-(nonafluoro-2-butyl) ethyl phenyl 2010 N C C C 2-(ethylsulfinyl)ethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2011 N C C C 2-fluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2012 N C C C 2,2-difluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2013 N C C C 2,2,2-trifluoroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2014 N C C C 1,3-difluoro-2-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2015 N C C C 1-chloro-3-fluoro-2-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2016 N C C C 1-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-(nonafluoro-2-butyl) ethyl phenyl 2017 N C C C 3,3,3-trifluoro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2018 N C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-(nonafluoro-2-butyl) propyl phenyl 2019 N C C C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2020 N C C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4-(nonafluoro-2-butyl) cyclobutyl phenyl 2021 N C C C 2-chloroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2022 N C C C 2,2-dichloroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2023 N C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2024 N C C C 1,3-dichloro-2-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2025 N C C C 3-chloro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2026 N C C C 2-bromoethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2027 N C C C 3-bromo-n-propyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2028 N C C C 2-iodoethyl H 2,6-dimethyl-4-(nonafluoro-2-butyl) phenyl 2029 N C C C (6-chloropyridin-3-yl) H 2,6-dimethyl-4-(nonafluoro-2-butyl) methyl phenyl 2030 N C C C Et H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2031 N C C C i-Pr H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2032 N C C C vinyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2033 N C C C cyclobutyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2034 N C C C cyclopentyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2035 N C C C 3-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2036 N C C C 4-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2037 N C C C 2-cyanoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2038 N C C C 2-(methylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2039 N C C C 2-(ethylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2040 N C C C 1-methyl-2-(methylthio) H 2,6-dibromo4-(heptafluoro-n- ethyl propylthio)phenyl 2041 N C C C 2-(ethylsulfinyl)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2042 N C C C 2-fluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2043 N C C C 2,2-difluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2044 N C C C 2,2,2-trifluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2045 N C C C 1,3-difluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2046 N C C C 1-chloro-3-fluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2047 N C C C 1-methyl-2,2,2-trifluoro H 2,6-dibromo-4-(heptafluoro-n- ethyl propylthio)phenyl 2048 N C C C 3,3,3-trifluoro-n-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2049 N C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dibromo-4-(heptafluoro-n- propyl propylthio)phenyl 2050 N C C C 4,4,4-trifluoro-n-butyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2051 N C C C 2,2,3,3-tetrafluoro H 2,6-dibromo-4-(heptefluoro-n- cyclobutyl propylthio)phenyl 2052 N C C C 2-chloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2053 N C C C 2,2-dichloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2054 N C C C 2,2,2-trichloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2055 N C C C 1,3-dichloro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2056 N C C C 3-chloro-n-propyl H 2,6-dibromo-4-(heptafluoro-n propylthio)phenyl 2057 N C C C 2-bromoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2058 N C C C 3-bromo-n-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2059 N C C C 2-iodoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2060 N C C C (6-chloropyridin-3-yl) H 2,6-dibromo-4-(heptafluoro-n- methyl propylthio)phenyl 2061 N-oxide C C C i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2062 N-oxide C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2063 N-oxide C C C Et H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2064 N-oxide C C C vinyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2065 N-oxide C C C cyclobutyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2066 N-oxide C C C cyclopentyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2067 N-oxide C C C 3-cyanobenzyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2068 N-oxide C C C 4-cyanobenzyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2069 N-oxide C C C 2-cyanoethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2070 N-oxide C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2071 N-oxide C C C 2-(ethylthio)ethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2072 N-oxide C C C 1-methyl-2-(methylthio)ethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2073 N-oxide C C C 2-(ethylsulfinyl)ethyl H 2,6-dimethyl-4-hepcafluoro isopropylphenyl 2074 N-oxide C C C 2-fluoroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2075 N-oxide C C C 2,2-difluoroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2076 N-oxide C C C 2,2,2-trifluoroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2077 N-oxide C C C 1,3-difluoro-2-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2078 N-oxide C C C 1-chloro-3-fluoro-2-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2079 N-oxide C C C 1-methyl-2,2,2-trifluoroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2080 N-oxide C C C 3,3,3-trifluoro-n-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2081 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-heptafluoro propyl isopropylphenyl 2082 N-oxide C C C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2083 N-oxide C C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4-heptafluoro cyclobutyl isopropylphenyl 2084 N-oxide C C C 2-chloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2085 N-oxide C C C 2,2-dichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2086 N-oxide C C C 1,3-dichloro-2-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2087 N-oxide C C C 3-chloro-n-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2088 N-oxide C C C 2-bromoethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2089 N-oxide C C C 3-bromo-n-propyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2090 N-oxide C C C 2-iodoethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2091 N-oxide C C C (6-chloropyridin-3-yl) H 2,6-dimethyl-4-heptafluoro methyl isopropylphenyl 2092 N-oxide C C C Et H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2093 N-oxide C C C i-Pr H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2094 N-oxide C C C vinyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2095 N-oxide C C C cyclobutyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2096 N-oxide C C C cyclopentyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2097 N-oxide C C C 3-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2098 N-oxide C C C 4-cyanobenzyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2099 N-oxide C C C 2-cyanoethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2100 N-oxide C C C 2-(methylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2101 N-oxide C C C 2-(ethylthio)ethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2102 N-oxide C C C 1-methyl-2-(methylthio) H 2,6-dimethyl-4-(nonafluoro-2- ethyl butyl)phenyl 2103 N-oxide C C C 2-(ethylsulfinyl)ethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2104 N-oxide C C C 2-fluoroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2105 N-oxide C C C 2,2-difluoroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2106 N-oxide C C C 2,2,2-trifluoroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2107 N-oxide C C C 1,3-difluoro-2-propyl H 2,6-dimethyl-4-nonafluoro-2- butyl)phenyl 2108 N-oxide C C C 1-chloro-3-fluoro-2-propyl H 2,6-dimethyl-4-nonafluoro-2- butyl)phenyl 2109 N-oxide C C C 1-methyl-2,2,2-trifluoro H 2,6-dimethyl-4-(nonafluoro-2- ethyl butyl)phenyl 2110 N-oxide C C C 3,3,3-trifluoro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2111 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dimethyl-4-(nonafluoro-2- propyl butyl)phenyl 2112 N-oxide C C C 4,4,4-trifluoro-n-butyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2113 N-oxide C C C 2,2,3,3-tetrafluoro H 2,6-dimethyl-4-(nonafluoro-2- cyclobutyl butyl)phenyl 2114 N-oxide C C C 2-chloroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2115 N-oxide C C C 2,2-dichloroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2116 N-oxide C C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2117 N-oxide C C C 1,3-dichloro-2-propyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2118 N-oxide C C C 3-chloro-n-propyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2119 N-oxide C C C 2-bromoethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2120 N-oxide C C C 3-bromo-n-propyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2121 N-oxide C C C 2-iodoethyl H 2,6-dimethyl-4-(nonafluoro-2- butyl)phenyl 2122 N-oxide C C C (6-chloropyridin-3-yl) H 2,6-dimethyl-4-(nonafluoro-2- methyl butyl)phenyl 2123 N-oxide C C C Et H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2124 N-oxide C C C i-Pr H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2125 N-oxide C C C vinyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2126 N-oxide C C C cyclobutyl H 2,6-dibromo-4-(heprafluoro-n- propylthio)phenyl 2127 N-oxide C C C cyclopentyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2128 N-oxide C C C 3-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2129 N-oxide C C C 4-cyanobenzyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2130 N-oxide C C C 2-cyanoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2131 N-oxide C C C 2-(methylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2132 N-oxide C C C 2-(ethylthio)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2133 N-oxide C C C 1-methyl-2-(methylthio) H 2,6-dibromo-4-(heptafluoro-n- ethyl propylthio)phenyl 2134 N-oxide C C C 2-(ethylsulfinyl)ethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2135 N-oxide C C C 2-fluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2136 N-oxide C C C 2,2-difluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2137 N-oxide C C C 2,2,2-trifluoroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2138 N-oxide C C C 1,3-difluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2139 N-oxide C C C 1-chloro-3-fluoro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2140 N-oxide C C C 1-methyl-2,2,2-trifluoro H 2,6-dibromo-4-(heptafluoro-n- ethyl propylthio)phenyl 2141 N-oxide C C C 3,3,3-trifluoro-n-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2142 N-oxide C C C 2,2,3,3,3-pentafluoro-n- H 2,6-dibromo-4-(heptafluoro-n- propyl propylthio)phenyl 2143 N-oxide C C C 4,4,4-trifluoro-n-butyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2144 N-oxide C C C 2,2,3,3-tetrafluoro H 2,6-dibromo-4-(heptafluoro-n- cyclobutyl propylthio)phenyl 2145 N-oxide C C C 2-chloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2146 N-oxide C C C 2,2-dichloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2147 N-oxide C C C 2,2,2-trichloroethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2148 N-oxide C C C 1,3-dichloro-2-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2149 N-oxide C C C 3-chloro-n-propyl H 2,6-dibromo-4-(heptatluoro-n- propylthio)phenyl 2150 N-oxide C C C 2-bromoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2151 N-oxide C C C 3-bromo-n-propyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2152 N-oxide C C C 2-iodoethyl H 2,6-dibromo-4-(heptafluoro-n- propylthio)phenyl 2153 N-oxide C C C (6-chloropyridin-3-yl) H 2,6-dibromo-4-(heptafluoro-n- methyl propylthio)phenyl 2154 C N C C i-Pr H 2-methyl-4- heptafluoroisopropylphenyl 2155 C N C C 2,2,2-trichloroethyl H 2-methyl-4- heptatluoroisopropylphenyl 2156 C N C C i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2157 C N C C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2158 C C N C i-Pr H 2-methyl-4-heptafluoro isopropylphenyl 2159 C C N C 2,2,2-trichloroethyl H 2-methyl-4-heptafluoro isopropylphenyl 2160 C C N C i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2161 C C N C 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2162 C C C N i-Pr H 2-methyl-4-heptafluoro isopropylphenyl 2163 C C C N 2,2,2-trichloroethyl H 2-methyl-4-heptafluoro isopropylphenyl 2164 C C C N i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2165 C C C N 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2166 C C C N-oxide i-Pr H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2167 C C C N-oxide 2,2,2-trichloroethyl H 2,6-dimethyl-4-heptafluoro isopropylphenyl 2168 N C C C 2,2,2-trichloroethyl Me 2,6-dimethyl-4-heptafluoro isopropylphenyl

TABLE 6 (4-A)

Compound No. R₃ Y₁ Y₂ Y₃ Y₄ Y₅ I-1  H Me H heptafluoro-n-propyl H Me I-2  H H H heptafluoroisopropyl H H I-3  H H Me heptafluoroisopropyl H H I-4  H H MeO heptafluoroisopropyl H H I-5  H H Cl heptafluoroisopropyl H H I-6  H Me H heptafluoroisopropyl H H I-7  H Me H heptafluoroisopropyl H Me I-8  H Me H heptafluoroisopropyl H phenyl I-9  H Me H heptafluoroisopropyl Me H I-10 H Me Me heptafluoroisopropyl H H I-11 H Me Me heptafluoroisopropyl H Cl I-12 H Me I heptafluoroisopropyl H Cl I-13 Me Me H heptafluoroisopropyl H Me I-14 i-Pr Me H heptafluoroisopropyl H Me I-15 H Et H heptafluoroisopropyl H H I-16 H Et H heptafluoroisopropyl H Me I-17 H Et H heptafluoroisopropyl H Et I-18 H Et H heptafluoroisopropyl H I I-19 H n-Pr H heptafluoroisopropyl H H I-20 H i-Pr H heptafluoroisopropyl H Me I-21 H MeO H heptafluoroisopropyl H Me I-22 H Cl H heptafluoroisopropyl H Et I-23 H Cl H heptafluoroisopropyl Me H I-24 H Cl H heptafluoroisopropyl MeO H I-25 H Cl Me heptafluoroisopropyl H Me I-26 H Br H heptafluoroisopropyl H Me I-27 H Br H heptafluoroisopropyl H Et I-28 H Br H heptafluoroisopropyl H n-Pr I-29 H Br H heptafluoroisopropyl H n-Bu I-30 H Br Me heptafluoroisopropyl H Me I-31 H I H heptafluoroisopropyl H Me I-32 H I H heptafluoroisopropyl H n-Pr I-33 H Me H nonafluoro-n-butyl H Me I-34 H Me H nonafluoro-2-butyl H Me I-35 H H H trifluoromethylthio H H I-36 H Br H trifluoromethylthio H Br I-37 H H H trifluoromethylsulfonyl H H I-38 H Br H trifluoromethyisulfonyl H Br I-39 H Me H 2,2,2-trifluoroethoxy H H I-40 H H H heptafluoroisopropylthio H H I-41 H Cl H heptafluoroisopropylthio H Cl I-42 H Br H heptafluoroisopropylthio H Br I-43 H Cl H heptafluoro-n-propylthio H Cl I-44 H Br H heptafluoro-n-propylthio H Br I-45 H Cl H heptafluoroisopropylsulfonyl H Cl I-46 H Br H nonafluoro-n-butylthio H Br I-47 H Br H pentafluoroethylthio H Br I-48 H Br H heptafluoro-n-propylsulfinyl H Br I-49 Me Me H heptafluoro-n-propylthio H Me I-50 Me Br H heptafluoro-n-propylthio H Br

TABLE 7 (4-B)

Compound No. X₁ X₂ X₃ X₄ Y₁ Y₃ Y₅ I-51 Me H H H Me heptafluoroisopropyl H I-52 Me H H H Me heptafluoroisopropyl Me I-53 H Me H H Me heptafluoroisopropyl H I-54 H Me H H Me heptafluoroisopropyl Me I-55 H H H Me Me heptafluoroisopropyl H I-56 H H H Me Me heptafluoroisopropyl Me I-59 F H H H Me heptafluoroisopropyl Me I-60 F H H H Me heptafluoroisopropylthio Me I-61 H F H H Me heptafluoroisopropyl Me I-62 H H H F Me heptafluoroisopropyl H I-63 H H H F Me heptafluoroisopropyl Me I-64 Cl H H H Me heptafluoroisopropyl H I-65 Cl H H H Me heptafluoroisopropyl Me I 66 H Cl H H Me heptafluoroisopropyl H I-67 H Cl H H Me heptafluoroisopropyl Me I-68 H H H Cl Me heptafluoroisopropyl H I-69 H H H Cl Me heptafluoroisopropyl Me I-70 Br H H H Me heptafluoroisopropyl Me I-71 H H H Br Me heptafluoroisopropyl H I-72 H I H H Me heptafluoroisopropyl H I-73 H H H I Me heptafluoroisopropyl H I-74 H H H I Me heptafluoroisopropyl Me I-75 H H CF₃ H Me heptafluoroisopropyl H I-76 H H CF₃ H Me heptafluoroisopropyl Me I-77 H MeO H H Me heptafluoroisopropyl H I-78 H H NH₂ H Me heptafluoroisopropyl H I-79 H H NH₂ H Me heptafluoroisopropyl Me I-80 Cl Cl H Cl Me heptafluoroisopropyl H

TABLE 8 (4-C)

Compound No. X₁ X₂ X₃ X₄ Q I-81 H H H H 2-methyl-4-heptafluoroisopropyl-1-naphthyl I-82 H H H H 4-heptafluoroisopropyl-5,6,7,8-tetrahydro-1-naphthyl I-83 H H H H 2-chloro-4-heptafluoroisopropyl-5,6,7,8,s-tetrahydro-1-naphthyl I-84 H H H H 2-((1,1,1,3,3,3-hexafluoro2-propyloxy)pyridin-5-yl I-85 Cl H H H 2-(1,1,1,3,3,3-hexafluoro-2-propyloxy)-4-methylpyridin-5-yl I-86 H H H H 2-bromo-4-methyl-6-(1,1,1,3,3,3-hexafluoro- 2-propyloxy)pyridin-3-yl

Table 9 shows the physical properties of the compounds represented by formulae (1) and (4) of the present invention. This table also shows ¹H-NMR shift values obtained by using tetramethylsilane as an internal reference material, and chloroform-d as a solvent. TABLE 9 Compound No. ¹H-NMR(CDCl₃, ppm) 3 δ 1.30(6H, d, J=6.3Hz), 2.41(3H, s), 5.00-5.05(1H, m), 6.92(1H, s), 7.40-7.61(5H, m), 7.93(1H, s), 8.01(1H, s), 8.21(1H, d, J=8.8Hz) 4 δ 0.96(3H, t, J=7.3Hz), 1.38-1.47(2H, m), 1.63-1.71(2H, m), 2.41(3H, s), 4.19(2H, t, J=6.6Hz), 6.83(1H, s), 7.42-7.62(5H, m), 7.83(1H, s), 8.00(1H, s), 8.25(1H, d, J=8.5Hz) 5 δ 0.98(6H, d, J=6.8Hz), 1.94-2.05(1H, m), 2.42(3H, s), 3.98(2H, d, J=6.6Hz), 6.81(1H, s), 7.44-7.52(3H, m), 7.55-7.61(2H, m), 7.85(1H, s), 8.01(1H, s), 8.25(1H, d, J=8.6Hz) 6 δ 0.96(3H, t, J=7.6Hz), 1.29(3H, d, J=6.1Hz), 1.58-1.73(2H, m), 2.42(3H, s), 4.83-4.92(1H, m), 6.72(1H, s), 7.42-7.61(5H, m), 7.79(1H, s), 8.01(1H, s), 8.26(1H, d, J=8.5Hz) 7 δ 1.53(9H, s), 2.41(3H, s), 6.66(1H, s), 7.40-7.59(5H, m), 7.80(1H, s), 7.98(1H, d, J=1.7Hz), 8.23(1H, d, J=8.8Hz) 8 δ 0.98(9H, s), 2.41(3H, s), 3.89(2H, s), 6.94(1H, s), 7.41-7.50(3H, m), 7.54-7.57(1H, m), 7.62(1H, d, J=8.1Hz), 7.86(1H, s), 8.02(1H, s), 8.24(1H, d, J=8.8Hz) 9 δ 0.97(9H, s), 1.62(2H, t, J=7.6Hz), 2.41(3H, s), 4.25(2H, t, J=7.6Hz), 6.79(1H, br), 7.42-7.51(3H, m), 7.54-7.57(1H, m), 7.61(1H, d), 7.82(1H, s), 7.99(1H, s), 8.24(1H, d, J=8.5Hz) 10 δ 0.90(3H, t, J=7.3Hz), 0.91(3H, t, J=7.3Hz), 1.26-1.41(8H, m), 1.55-1.65(1H, m), 2.40(3H, s), 4.10(2H, t, J=5.4Hz), 7.01(1H, s), 7.40-7.50(3H, m), 7.55(1H, d, J=7.8Hz), 7.62(1H, d, J=7.8Hz), 7.91(1H, s), 8.01(1H, s), 8.21(1H, d, J=8.5Hz) 11 δ 2.42(3H, s), 4.55(1H, dd, J=1.7Hz, 6.3Hz), 4.83(1H, dd, J=1.7Hz, 13.9Hz), 7.29(1H, dd, J=6.3Hz, 13.9Hz), 7.42-7.50(3H, m), 7.61-7.63(1H, m), 7.77(1H, d, J=7.8Hz), 8.08(1H, s), 8.15(1H, d, J=7.8Hz), 8.30(1H, s), 8.92(1H, br-s) 12 δ 2.42(3H, s), 4.68-4.70(2H, m), 5.27-5.31(1H, m), 5.35-5.41(1H, m), 5.93-6.03(1H, m), 6.83(1H, br), 7.44-7.52(3H, m), 7.55-7.63(2H, m), 7.79(1H, br), 8.00(1H, s), 8.26(1H, d, J=8.8Hz) 13 δ 0.82(3H, d, J=7.1Hz), 0.84-0.99(7H, m), 1.02-1.12(2H, m), 1.36-1.42(1H, m), 1.50-1.59(1H, m), 1.68-1.72(2H, m), 1.94-1.99(1H, m), 2.11(1H, d, J=1.7Hz), 2.42(3H, s), 4.65-4.72(1H, m), 6.74(1H, s), 7.42-7.62(5H, m), 7.80(1H, s), 8.02(1H, s), 8.25(1H, d, J=8.5Hz) 14 δ 2.38(3H, s), 5.19(2H, s), 7.19(1H, s), 7.32-7.61(10H, m), 7.91(1H, s), 8.00(1H, s), 8.18(1H, d, J=8.5Hz) 16 δ 2.34(3H, s), 5.27(2H, s), 6.96(1H, br-s), 7.40-7.58(6H, m), 7.63-7.69(3H, m), 7.79(1H, s), 8.00(1H, s), 8.25(1H, d, J=8.8Hz) 17 δ 2.33(3H, s), 3.34(3H, s), 3.57-3.61(2H, m), 4.26-4.32(2H, m), 7.13(1H, s), 7.32-7.42(3H, m), 7.46-7.53(2H, m), 7.83(1H, s), 7.91(1H, d, J=1.7Hz), 8.13(1H, d, J=8.5Hz) 18 δ 2.42(3H, s), 5.83(2H, s), 7.16(1H, br-s), 7.43-7.52(3H, m), 7.61(1H, d, J=8.1Hz), 7.68(1H, d, J=8.1Hz), 7.82(1H, s), 8.03(1H, s), 8.25(1H, d, J=8.5Hz) 18 δ 2.42(3H, s), 5.83(2H, s), 7.16(1H, br-s), 7.43-7.52(3H, m), 7.61(1H, d, J=8.1Hz), 7.68(1H, d, J=8.1Hz), 7.82(1H, s), 8.03(1H, s), 8.25(1H, d, J=8.5Hz) 19 δ 2.40(3H, s), 3.74(2H, t, J=5.6Hz), 4.44(2H, t, J=5.6Hz), 7.19(1H, s), 7.42-7.50(3H, m), 7.55-7.58(1H, m), 7.63(1H, d, J=7.6Hz), 7.88(1H, s), 8.01(1H, s), 8.22(1H, d, J=8.8Hz) 20 δ 2.40(3H, s), 4.83(2H, s), 7.42-7.49(3H, m), 7.58-7.61(1H, m), 7.67-7.69(2H, m), 7.98(1H, s), 8.06(1H, s), 8.19(1H, d, J=8.5Hz) 21 δ 2.43(3H, s), 6.90(1H, s), 7.22(1H, br-s), 7.47-7.54(3H, m), 7.64-7.68(2H, m), 7.78(1H, s), 8.06(1H, s), 8.26(1H, d, J=8.8Hz) 22 δ 2.01(6H, s), 2.42(3H, s), 6.95(1H, br), 7.44-7.52(3H, m), 7.57-7.62(2H, m), 7.80(1H, s), 8.02(1H, s), 8.24(1H, d, J=8.5Hz) 23 δ 2.41(3H, s), 7.23-7.29(1H, m), 7.40-7.55(7H, m), 7.61-7.64(1H, m), 7.72(1H, d, J=8.3Hz), 7.78(1H, s), 8.07(1H, s), 8.26(1H, d, J=8.8Hz) 24 δ 2.36(3H, s), 2.40(3H, s), 7.05-7.09(2H, m), 7.15(1H, s), 7.20(2H, d, J=8.1Hz), 7.47-7.52(3H, m), 7.60-7.63(1H, m), 7.66-7.68(1H, m), 7.79(1H, s), 8.07(1H, s), 8.25(1H, d, J=8.8Hz) 25 δ 2.41(3H, s), 7.12-7.17(2H, m), 7.32-7.38(2H, m), 7.42-7.48(3H, m), 7.64(1H, d, J=7.8Hz), 7.82(1H, d, J=7.8Hz), 7.99(1H, d, J=8.5Hz), 8.06(1H, d, J=8.5Hz), 8.51(1H, s), 9.52(1H, s) 59 δ 2.32(6H, s), 3.79(3H, s), 6.92(1H, br-s), 7.34(2H, s), 7.43(1H, t, J=7.8Hz), 7.52-7.62(3H, m), 8.00(1H, s) 60 δ 1.33(3H, t, J=7.1Hz), 2.33(6H, s), 4.24(2H, q, J=7.1Hz), 6.80(1H, s), 7.35(2H, s), 7.44(1H, t, J=7.8Hz), 7.46(1H, s), 7.52-7.61(2H, m), 8.02(1H, s) 61 δ 0.99(3H, t, J=7.3Hz), 1.71(2H, m), 2.34(6H, s), 4.14(2H, t, J=6.9Hz), 6.79(1H, s), 7.35(2H, s), 7.41-7.47(2H, m), 7.59-7.61(2H, m), 8.02(1H, s) 62 δ 1.31(6H, d, J=6.3Hz), 2.33(6H, s), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.35(2H, s), 7.43(1H, t, J=8.1Hz), 7.52(1H, s), 7.56-7.61(2H, m), 8.03(1H, s) 63 δ 0.96(3H, t, J=7.3Hz), 1.38-1.48(2H, m), 1.61-1.71(2H, m), 2.34(6H, s), 4.19(2H, t, J=6.9Hz), 6.76(1H, s), 7.35(2H, s), 7.42-7.46(2H, m), 7.58-7.61(2H, m), 8.02(1H, s) 64 δ 0.98(6H, d, J=6.8Hz), 1.94-2.04(1H, m), 2.34(6H, s), 3.97(2H, d, J=6.6Hz), 6.79(1H, s), 7.35(2H, s), 7.42-7.47(2H, m), 7.59-7.61(2H, m), 8.02(1H, s) 66 δ 1.53(9H, s), 2.34(6H, s), 6.62(1H, s), 7.35(2H, s), 7.38-7.45(2H, m), 7.51-7.60(2H, m), 8.02(1H, s) 67 δ 0.99(9H, s), 2.34(6H, s), 3.90(2H, s), 6.79(1H, s), 7.35(2H, s), 7.43(1H, br-s), 7.46(1H, t, J=8.1Hz), 7.59-7.63(2H, m), 8.03(1H, s) 68 δ 0.95(3H, d, J=6.8Hz), 0.96(3H, d, J=6.8Hz), 1.24(3H, d, J=6.3Hz), 1.81-1.89(1H, m), 2.34(6H, s), 4.75(1H, quint, J=6.3Hz), 6.77(1H, s), 7.35(2H, s), 7.44(1H, t, J=8.1Hz), 7.54-7.62(3H, m), 8.05(1H, s) 69 δ 0.94(3H, t, J=7.3Hz), 1.29(3H, d, J=6.3Hz), 1.32-1.45(2H, m), 1.46-1.58(1H, m), 1.61-1.70(1H, m), 2.35(6H, s), 4.93(1H, sext., J=6.3Hz), 6.73(1H, s), 7.35(2H, s), 7.42-7.47(1H, m), 7.51(1H, s), 7.56-7.62(2H, m), 8.05(1H, s) 70 δ 0.93(3H, d, J=6.6Hz), 0.94(3H, d, J=6.6Hz), 1.29(3H, d, J=6.3Hz), 1.31-1.37(1H, m), 1.57-1.75(2H, m), 2.34(6H, s), 4.96-5.05(1H, m), 6.70(1H, s), 7.35(2H, s), 7.42-7.46(2H, m), 7.57-7.61(2H, m), 8.04(1H, s) 71 δ 0.97(9H, s), 1.62(2H, t, J=7.6Hz), 2.34(6H, s), 4.25(2H, t, J=7.6Hz), 6.73(1H, s), 7.35(2H, s), 7.43-7.47(2H, m), 7.59-7.61(2H, m), 8.02(1H, s) 72 δ 1.27-1.34(2H, m), 1.50-1.66(4H, m), 1.74-1.83(2H, m), 2.18-2.32(1H, m), 2.34(6H, s), 4.07(2H, d, J=7.1Hz), 6.79(1H, s), 7.35(2H, s), 7.43-7.51(2H, m), 7.58-7.62(2H, m), 8.03(1H, s) 73 δ 1.62(3H, d, J=6.6Hz), 2.33(6H, s), 5.90(1H, q, J=6.6Hz), 6.82(1H, br-s), 7.28-7.45(9H, m), 7.56(1H, d, J=8.1Hz), 7.60(1H, d, J=7.6Hz), 8.02(1H, br-s) 74 δ 2.34(6H, s), 3.02(2H, t, J=7.1Hz), 4.42(2H, t, J=7.1Hz), 6.74(1H, br-s), 7.23-7.27(2H, m), 7.31-7.35(5H, m), 7.41-7.47(2H, m), 7.58-7.62(2H, m), 7.99(1H, br-s) 75 δ 2.34(6H, s), 4.58(1H, dd, J=2.0Hz, 6.3Hz), 4.87(1H, dd, J=2.0Hz, 13.9Hz), 7.00(1H, s), 7.25(1H, dd, J=6.3Hz, 13.9Hz), 7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.55(1H, s), 7.63-7.65(2H, m), 8.03(1H, s) 76 δ 2.34(6H, s), 4.68-4.70(2H, m), 5.26-5.31(1H, m), 5.35-5.41(1H, m), 5.92-6.02(1H, m), 6.84(1H, s), 7.35(2H, s), 7.42-7.47(2H, m), 7.60-7.62(2H, m), 8.02(1H, s) 77 δ 2.33(6H, s), 2.53(1H, t, J=1.4Hz), 4.79(2H, d, J=1.4Hz), 6.97(1H, br-s), 7.35(2H, s), 7.44(1H, t, J=8.1Hz), 7.51(1H, s), 7.59-7.63(2H, m), 8.02(1H, s) 78 δ 1.60-1.70(1H, m), 1.78-1.86(1H, m), 2.07-2.18(2H, m), 2.33(6H, s), 2.35-2.43(2H, m), 5.00-5.08(1H, m), 6.80(1H, s), 7.35(2H, s), 7.41-7.46(1H, m), 7.53-7.62(3H, m), 8.03(1H, s) 79 δ 1.68-1.80(6H, m), 1.86-1.94(2H, m), 2.34(6H, s), 5.20-5.23(1H, m), 6.72(1H, s), 7.35(2H, s), 7.42-7.62(4H, m), 8.04(1H, s) 81 δ 2.32(6H, s), 5.22(2H, s), 6.87(1H, s), 7.34(2H, s), 7.36-7.45(7H, m), 7.57-7.61(2H, m), 8.01(1H, s) 82 δ 2.33(9H, s), 5.18(2H, s), 6.83(1H, br-s), 7.14-7.20(3H, m), 7.31(1H, d, J=7.8Hz), 7.35(2H, s), 7.44(2H, t, J=7.8Hz), 7.52-7.62(2H, m), 8.01(1H, br-s) 83 δ 2.34(6H, s), 5.28(2H, s), 6.90(1H, br-s), 7.35(2H, s), 7.43-7.54(4H, m), 7.61-7.66(4H, m), 8.01(1H, s) 84 δ 2.34(6H, s), 5.24(2H, s), 6.92(1H, br-s), 7.35-7.52(4H, m), 7.63-7.81(6H, m), 8.02(1H, s) 85 δ 2.34(6H, s), 5.27(2H, s), 6.97(1H, br-s), 7.35(2H, s), 7.45-7.52(4H, m), 7.61-7.69(4H, m), 8.01(1H, s) 89 δ 2.34(6H, s), 5.34(2H, s), 6.90(1H, br), 7.28-7.30(3H, m), 7.35(2H, s), 7.39-7.49(3H, m), 7.59-7.64(2H, m), 8.04(1H, m) 90 δ 2.33(6H, s), 5.18(2H, s), 6.92(1H, s), 7.22-7.34(5H, m), 7.40-7.47(3H, m), 7.59-7.63(2H, m), 8.02(1H, s) 91 δ 2.33(6H, s), 5.18(2H, s), 6.86(1H, s), 7.29-7.38(6H, m), 7.43-7.47(2H, m), 7.60-7.62(2H, m), 8.01(1H, s) 92 δ 2.34(6H, s), 5.32(2H, s), 6.92(1H, br-s), 7.36(2H, s), 7.42(1H, s), 7.48(1H, t, J=7.8Hz), 7.58(2H, d, J=9.0Hz), 7.62-7.66(2H, m), 8.01(1H, s), 8.25(2H, d, J=9.0Hz) 93 δ 2.35(6H, s), 3.93(3H, s), 5.28(2H, s), 6.88(1H, br-s), 7.36(2H, s), 7.41(1H, s), 7.45-7.49(4H, m), 7.63(2H, d, J=6.8Hz), 8.02(1H, s), 8.05(1H, d, J=6.8Hz) 94 δ 2.32(6H, s), 2.62(1H, br), 3.87(2H, t, J=4.4Hz), 4.29-4.32(2H, m), 7.26(1H, s), 7.34(2H, s), 7.42(1H, t, J=8.1Hz), 7.54-7.61(2H, m), 7.77(1H, s), 8.00(1H, s) 95 δ 2.31(6H, s), 3.41(3H, s), 3.64-3.66(2H, m), 4.32-4.35(2H, m), 7.14(1H, s), 7.34(2H, s), 7.40(1H, t, J=7.8Hz), 7.55-7.60(2H, m), 7.67(1H, s), 8.00(1H, s) 96 δ 1.23(3H, t, J=6.8Hz), 2.29(6H, s), 3.56(2H, q, J=6.8Hz), 3.67-3.70(2H, m), 4.31-4.34(2H, m), 7.26(1H, s), 7.33(2H, s), 7.38-7.40(1H, m), 7.52-7.60(2H, m), 7.83(1H, s), 8.00(1H, s) 97 δ 1.18(6H, d, J=6.1Hz), 2.29(6H, s), 3.63-3.69(3H, m), 4.30-4.32(2H, m), 7.26(1H, s), 7.33(2H, s), 7.38(1H, t, J=7.8Hz), 7.56-7.60(2H, m), 7.82(1H, s), 8.00(1H, s) 98 δ 2.28(6H, s), 3.70-3.73(2H, m), 4.33-4.36(2H, m), 4.57(2H, s), 7.23-7.39(9H, m), 7.53(1H, d, J=7.8Hz), 7.58(1H, d, J=7.8Hz), 7.87(1H, s), 7.99(1H, s) 99 δ 1.20(3H, t, J=8.1Hz), 1.95-2.00(2H, m), 2.35(6H, s), 3.47-3.57(4H, m), 4.30(2H, t, J=6.6Hz), 6.78(1H, s), 7.35(2H, s), 7.46(2H, t, J=7.8Hz), 7.61(2H, d, J=7.8Hz), 8.02(1H, s) 100 δ 1.30(3H, t, J=7.3Hz), 2.34(6H, s), 4.26(2H, q, J=7.3Hz), 4.72(2H, s), 7.35(2H, s), 7.36-7.40(1H, m), 7.52-7.60(3H, m), 7.77-7.79(1H, m), 7.90(1H, br-s) 101 δ 1.56(3H, d, J=7.3Hz), 2.33(6H, s), 3.79(3H, s), 5.18(1H, q, J=7.3Hz), 7.21(1H, br), 7.35(2H, s), 7.41(1H, t, J=7.8Hz), 7.55-7.62(3H, m), 7.98(1H, s) 102 δ 1.29(3H, t, J=6.8Hz), 1.55(3H, d, J=6.8Hz), 2.34(6H, s), 4.23(2H, q, J=6.8Hz), 5.16(1H, q, J=6.8Hz), 7.24(1H, br), 7.35(2H, s), 7.41(1H, t, J=7.8Hz), 7.55-7.62(3H, m), 7.96(1H, s) 103 δ 2.21(3H, s), 2.34(6H, s), 2.84(2H, t, J=6.1Hz), 4.46(2H, t, J=6.1Hz), 6.91(1H, br-s), 7.35(2H, s), 7.43(1H, t, J=7.8Hz), 7.52-7.70(3H, m), 8.01(1H, s) 104 δ 2.10(3H, s), 2.34(6H, s), 4.33-4.42(4H, m), 6.97(1H, br-s), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.57-7.64(3H, m), 8.01(1H, s) 106 δ 2.33(6H, s), 2.78(2H, t, J=6.3Hz), 4.40(2H, t, J=6.3Hz), 7.12(1H, br), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.60-7.65(3H, m), 8.01(1H, s) 108 δ 2.17(3H, s), 2.34(6H, s), 2.80(2H, t, J=6.6Hz), 4.37(2H, t, J=6.6Hz), 6.84(1H, br-s), 7.35(2H, s), 7.43-7.52(2H, m), 7.58-7.63(2H, m), 8.02(1H, s) 109 δ 1.25-1.31(3H, m), 2.33(6H, s), 2.57-2.64(2H, m), 2.81-2.85(2H, m), 4.32-4.38(2H, m), 6.92(1H, s), 7.35(2H, s), 7.42-7.49(1H, m), 7.58-7.63(3H, m), 8.03(1H, s) 110 δ 1.28(6H, d, J=6.6Hz), 2.34(6H, s), 2.84(2H, t, J=7.1Hz), 2.94-3.04(1H, m), 4.34(2H, t, J=7.1Hz), 6.88(1H, s), 7.35(2H, s), 7.42-7.49(1H, m), 7.52-7.64(3H, m), 8.02(1H, s) 111 δ 1.40(3H, d, J=6.1Hz), 2.17(3H, s), 2.34(6H, s), 2.67(1H, dd, J=6.1Hz, 13.7Hz), 2.77(1H, dd, J=6.1Hz, 13.7Hz), 5.08(1H, sextett., J=6.1Hz), 6.80(1H, s), 7.35(2H, s), 7.45(1H, t, J=7.8Hz), 7.52(1H, s), 7.57-7.63(2H, m), 8.04(1H, s) 112 δ 1.24-1.37(3H, m), 2.35(6H, s), 2.26-2.31(2H, m), 2.98-3.06(2H, m), 4.67-4.76(2H, m), 7.35(3H, s), 7.45(2H, t, J=7.8Hz), 7.55-7.74(2H, m), 8.08(1H, br-s) 113 δ 1.36-1.43(3H, m), 2.35(6H, s), 3.04-3.10(2H, m), 3.37(2H, t, J=5.9Hz), 4.68-4.73(2H, m), 7.00(1H, br-s), 7.35(2H, s), 7.46(2H, t, J=7.8Hz), 7.55-7.70(2H, m), 8.02-8.07(1H, m) 116 δ 2.35(6H, s), 4.45(2H, dt, J=28.3Hz, 4.0Hz), 4.66(2H, dt, J=47.3Hz, 4.0Hz), 6.88(1H, br-s), 7.36(2H, s), 7.46-7.50(2H, m), 7.59-7.65(2H, m), 8.02(1H, s) 117 δ 2.34(6H, s), 4.38(2H, dt, J=3.9Hz, 13.6Hz), 6.00(1H, tt, J=3.9Hz, 47.3Hz), 7.05(1H, br-s), 7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.57-7.66(3H, m), 8.01(1H, s) 118 δ 2.33(6H, s), 4.57(2H, q, J=8.3Hz), 7.09(1H, br), 7.35(2H, s), 7.45-7.50(2H, m), 7.61-7.66(2H, m), 8.01(1H, s) 119 δ 2.35(6H, s), 4.61-4.75(4H, m), 5.18-5.31(1H, m), 6.98(1H, br-s), 7.36(2H, s), 7.45-7.52(2H, m), 7.58-7.66(2H, m), 8.03(1H, s) 120 δ 2.35(6H, s), 3.75-3.83(2H, m), 4.46-4.80(2H, m), 5.19-5.24(1H, m), 6.97(1H, br-s), 7.36(2H, s), 7.36-7.48(2H, m), 7.60-7.66(2H, m), 8.03(1H, s) 121 (DMSO-d₆)δ 1.48(3H, d, J=6.6Hz), 2.35(6H, s), 5.35(1H, septet, J=6.6Hz), 7.33(2H, s), 7.42(1H, t, J=7.8Hz), 7.68(1H, d, J=7.8Hz), 7.76(1H, d, J=7.8Hz), 8.11(1H, s), 8.76(1H, s), 9.26(1H, s) 122 (CDCl₃+DMSO-d₆)δ 2.35(6H, s), 5.87(1H, septet, J=6.3Hz), 7.33(2H, s), 7.44(1H, t, J=8.1Hz), 7.71-7.78(2H, m), 8.17(1H, s), 8.97(1H, s), 10.19(1H, s) 123 δ 2.34(6H, s), 2.48-2.59(2H, m), 4.42(2H, t, J=6.3Hz), 6.93(1H, br- s), 7.35(2H, s), 7.46(1H, t, J=7.8Hz), 7.57-7.64(3H, m), 8.01(1H, br-s) 124 δ 2.35(6H, s), 4.67(2H, t, J=13.2Hz), 6.98(1H, br-s), 7.29(2H, s), 7.36(1H, s), 7.50(1H, t, J=7.8Hz), 7.65-7.67(2H, m), 8.01(1H, s) 125 δ 1.51(3H, d, J=6.4Hz), 2.35(6H, s), 5.49-5.50(1H, m), 6.90(1H, br- s), 7.36(2H, s), 7.44(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.62-7.67(2H, m), 8.02(1H, s) 126 δ 1.95-2.05(2H, m), 2.22-2.27(2H, m), 2.35(6H, s), 4.26(2H, t, J=6.4Hz), 6.81(1H, s), 7.36(2H, s), 7.45-7.49(2H, m), 7.61-7.63(2H, m), 8.02(1H, s) 127 δ 2.35(6H, s), 2.61-2.65(1H, m), 2.9-3.1(1H, m), 5.2-5.3(1H, m), 7.01(1H, br-s), 7.36(2H, s), 7.45-7.52(2H, m), 7.62-7.68(2H, m), 8.01(1H, s) 128 δ 2.34(6H, s), 5.84(2H, s), 7.03(1H, s), 7.36(2H, s), 7.44-7.52(2H, m), 7.65-7.67(2H, m), 8.04(1H, s) 129 δ 2.36(6H, s), 7.33(2H, s), 7.40-7.46(1H, m), 7.65(1H, d, J=7.8Hz), 7.90(1H, d, J=7.8Hz), 7.95(1H, d, J=1.7Hz), 8.55(1H, s), 9.07(1H, s) 130 δ 2.35(6H, s), 3.74-3.77(2H, m), 4.44-4.47(2H, m), 6.87(1H, br), 7.36(2H, s), 7.43-7.52(2H, m), 7.59-7.64(2H, m), 8.02(1H, s) 131 δ 2.32(6H, s), 4.53(2H, d, J=5.9Hz), 5.90(1H, t, J=5.9Hz), 7.11(1H, br-s), 7.35(2H, s), 7.45(1H, t, J=8.1Hz), 7.60-7.64(3H, m), 8.01(1H, br-s) 132 δ 2.33(6H, s), 4.84(2H, s), 7.29(1H, br), 7.35(2H, s), 7.47(1H, t, J=7.8Hz), 7.58(1H, s), 7.64-7.66(2H, m), 8.04(1H, s) 133 δ 2.35(6H, s), 6.90(1H, s), 7.17(1H, br), 7.36(2H, s), 7.42(1H, s), 7.50-7.54(1H, m), 7.66-7.71(2H, m), 8.06(1H, s) 134 δ 2.35(6H, s), 3.83(4H, d, J=5.1Hz), 5.22(1H, quint, J=5.1Hz), 6.93(1H, s), 7.36(2H, s), 7.43(1H, s), 7.48(1H, t, J=7.8Hz), 7.60-7.66(2H, m), 8.03(1H, s) 135 δ 2.01(6H, s), 2.35(6H, s), 6.88(1H, br), 7.36(2H, s), 7.43-7.52(2H, m), 7.58-7.65(2H, m), 8.03(1H, s) 136 δ 2.17(2H, quint, J=6.3Hz), 2.34(6H, s), 3.66(2H, t, J=6.3Hz), 4.36(2H, t, J=6.3Hz), 6.83(1H, s), 7.35(2H, s), 7.43-7.48(1H, m), 7.52(1H, s), 7.59-7.63(2H, m), 8.02(1H, s) 137 δ 2.35(6H, s), 3.59(2H, t, J=5.9Hz), 4.51(2H, t, J=5.9Hz), 6.86(1H, br), 7.36(2H, s), 7.43-7.52(2H, m), 7.60-7.64(2H, m), 8.02(1H, s) 138 δ 2.34(6H, s), 5.03(2H, s), 7.15(1H, br), 7.35(2H, s), 7.47-7.54(2H, m), 7.64-7.69(2H, m), 8.06(1H, s) 139 δ 2.25(2H, quint, J=6.1Hz), 2.34(6H, s), 3.51(2H, t, J=6.1Hz), 4.35(2H, t, J=6.1Hz), 6.83(1H, s), 7.35(2H, s), 7.46(1H, t, J=8.1Hz), 7.54(1H, s), 7.58-7.64(2H, m), 8.02(1H, s) 140 δ 2.34(6H, s), 3.34-3.39(2H, m), 4.42-4.47(2H, m), 6.91-6.99(1H, br), 7.35(2H, s), 7.43-7.49(1H, m), 7.56-7.64(3H, m), 8.03(1H, s) 141 (DMSO-d₆)δ 1.82(3H, s), 2.28(6H, s), 3.33(2H, q, J=5.9Hz), 4.11(2H, t, J=5.9Hz), 7.44(2H, s), 7.46(1H, d, J=7.8Hz), 7.62-7.69(2H, m), 8.04(1H, t, J=5.9Hz), 8.09(1H, s), 9.90(1H, s), 9.93(1H, s) 146 δ 2.34(6H, s), 2.36(3H, s), 7.05-7.08(2H, m), 7.17-7.20(2H, m), 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.68(1H, d, J=7.8Hz), 7.80(1H, d, J=7.8Hz), 8.17(1H, s), 8.67(1H, s), 9.29(1H, s) 147 δ 2.35(6H, s), 7.33(2H, s), 7.41-7.57(5H, m), 7.72(1H, d, J=7.8Hz), 7.82(1H, d, J=7.8Hz), 8.18(1H, s), 9.01(1H, s), 9.73(1H, s) 148 δ 2.35(6H, s), 7.13-7.18(2H, m), 7.32-7.37(4H, m), 7.41-7.45(1H, m), 7.70(1H, d, J=7.6Hz), 7.81(1H, d, J=7.6Hz), 8.16(1H, s), 9.04(1H, s), 9.69(1H, s) 149 δ 2.34(6H, s), 7.32(2H, s), 7.33-7.36(1H, m), 7.42-7.52(3H, m), 7.65(1H, d, J=2.4Hz), 7.70(1H, d, J=7.8Hz), 7.80-7.88(4H, m), 8.20(1H, s), 8.76(1H, s), 9.48(1H, s) 154 δ 2.08-2.14(1H, m), 2.18-2.30(1H, m), 2.35(6H, s), 3.86-4.01(4H, m), 5.37-5.39(1H, m), 6.87(1H, br-s), 7.35(2H, s), 7.46(2H, t, J=7.6Hz), 7.58-7.63(2H, m), 8.01(1H, s) 155 δ 2.34(6H, s), 5.18(2H, s), 6.38(1H, d, J=3.2Hz), 6.48(1H, d, J=3.2Hz), 6.83(1H, br-s), 7.35(2H, s), 7.43-7.47(3H, m), 7.57-7.63(2H, m), 8.01(1H, s) 156 δ 2.34(6H, s), 5.10(2H, s), 6.48(1H, s), 6.79(1H, br-s), 7.35(2H, s), 7.39-7.47(3H, m), 7.53(1H, s), 7.59-7.63(2H, m), 8.01(1H, br-s) 157 δ 1.58-1.67(1H, m), 1.93-1.95(2H, m), 2.01-2.09(1H, m), 2.34(6H, s), 3.78-3.93(2H, m), 4.06-4.23(2H, m), 4.31(1H, dd, J=3.2Hz, 11.2Hz), 6.95(1H, br-s), 7.35(2H, s), 7.45(2H, t, J=7.8Hz), 7.50-7.56(1H, m), 7.63(1H, d, J=7.1Hz), 8.04(1H, s) 158 δ 1.66-1.73(1H, m), 2.05-2.13(1H, m), 2.34(6H, s), 2.60-2.70(1H, m), 3.64-3.68(1H, m), 3.73-3.79(1H, m), 3.85-3.92(2H, m), 4.09-4.15(2H, m), 6.87(1H, br-s), 7.35(2H, s), 7.46(2H, t, J=7.8Hz), 7.61-7.66(2H, m), 8.01(1H, br-s) 159 δ 2.34(6H, s), 5.38(2H, s), 6.83(1H, br-s), 6.98-7.02(1H, m), 7.16(1H, d, J=2.9Hz), 7.34-7.36(3H, m), 7.43-7.47(2H, m), 7.59-7.63(2H, m), 8.01(1H, s) 160 δ 2.34(6H, s), 5.23(2H, s), 6.83(1H, br-s), 7.14(1H, d, J=5.1Hz), 7.33-7.37(4H, m), 7.45(2H, t, J=7.8Hz), 7.61-7.64(2H, m), 8.02(1H, s) 161 δ 2.32(6H, s), 5.34(2H, s), 7.24-7.28(2H, m), 7.35(2H, s), 7.39(1H, d, J=7.8Hz), 7.43(1H, d, J=7.8Hz), 7.55(1H, s), 7.61(2H, t, J=7.8Hz), 7.73(1H, dt, J=1.7Hz, 7.8Hz), 8.03(1H, s), 8.61(1H, br-s) 162 δ 2.36(6H, s), 5.36(2H, s), 6.37(1H, br-s), 6.70(1H, s), 7.31-7.39(4H, m), 7.73-7.82(4H, m), 8.58-8.61(1H, m), 8.72(1H, d, J=2.0Hz) 163 δ 2.34(6H, s), 5.22(2H, s), 6.89(1H, br-s), 7.35-7.49(5H, m), 7.62(2H, d, J=7.3Hz), 7.72-7.77(1H, m), 8.00(1H, br-s), 8.45(1H, d, J=2.4Hz) 164 δ1.23(6H, d, J=6.8Hz), 2.34(3H, s), 3.18(1H, septet, J=6.8Hz), 3.81(3H, s), 6.84(1H, s), 7.36(1H, s), 7.42(1H, s), 7.46(1H, t, J=7.8Hz), 7.56-7.63(3H, m), 8.01(1H, s) 165 δ1.22(6H, d, J=6.8Hz), 1.33(3H, t, J=7.3Hz), 2.33(3H, s), 3.17(1H, septet, J=6.8Hz), 4.24(2H, q, J=7.3Hz), 6.80(1H, s), 7.35(1H, s), 7.41(1H, s), 7.44(1H, t, J=7.8Hz), 7.58-7.62(3H, m), 8.02(1H, s) 166 δ 1.32(6H, d, J=6.1Hz), 5.03(1H, septet, J=6.1Hz), 6.71(1H, s), 7.40-7.44(1H, m), 7.54(1H, d, J=2.0Hz), 7.56(1H, d, J=2.0Hz), 7.60(2H, d, J=8.8Hz), 7.80(2H, d, J=8.8Hz), 7.98(1H, s), 8.03(1H, s) 167 δ1.32(6H, d, J=6.1Hz), 2.53(3H, d, J=8.8Hz), 5.04(1H, septet, J=6.1Hz), 6.71(1H, br s), 7.41-7.65(6H, m), 7.95-7.97(2H, m) 168 δ 1.32(6H, d, J=6.1Hz), 1.33(3H, t, J=7.6Hz), 2.74(2H, q, J=7.6Hz), 5.04(1H, septet, J=6.1Hz), 6.70(1H, s), 7.43-7.56(4H, m), 7.60(1H, d, J=8.1Hz), 7.86(1H, s), 8.00(1H, s), 8.27(1H, d, J=8.5Hz) 169 δ 1.02(3H, t, J=7.3Hz), 1.32(6H, d, J=6.3Hz), 1.67-1.77(2H, m), 2.70(2H, t, J=7.3Hz), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.43-7.60(5H, m), 7.89(1H, s), 8.03(1H, s), 8.29(1H, d, J=8.5Hz) 170 δ1.32(6H, d, J=6.4Hz), 3.89(3H, s), 5.04(1H, septet, J=6.4Hz), 6.73(1H, br s), 7.05-7.08(1H, m), 7.42-7.46(1H, m), 7.51-7.58(3H, m), 7.80(1H, s), 8.00(1H, s), 8.15(1H, s) 171 δ1.32(6H, d, J=6.4Hz), 5.03(1H, septet, J=6.4Hz), 6.75(1H, s), 7.28-7.47(2H, m), 7.52-7.58(2H, m), 7.72-7.75(1H, m), 7.92(1H, s), 8.00(1H, s), 8.37(1H, s) 172 δ1.31(6H, d, J=6.3Hz), 2.30(3H, s), 2.47(3H, d, J=5.9Hz), 5.01-5.09(1H, m), 6.72(1H, br-s), 7.40-7.47(2H, m), 7.56-7.60(2H, m), 7.77(1H, d, J=8.6Hz), 7.83(1H, br-s), 8.00(1H, br-s) 173 δ 1.31(6H, d, J=6.1Hz), 2.35(3H, s), 2.52(3H, d, J=9.0Hz), 4.99-5.09(1H, m), 6.71(1H, br-s), 7.30(1H, br-s), 7.44(1H, t, J=7.8Hz), 7.52-7.57(1H, m), 7.61(1H, d, J=7.8Hz), 7.72(1H, s), 7.98(1H, s), 8.06(1H, s) 174 δ 1.23(6H, t, J=7.6Hz), 1.32(6H, d, J=6.1Hz), 2.69(4H, q, J=7.6Hz), 5.03(1H, septet, J=6.1Hz), 6.70(1H, s), 7.38(2H, s), 7.42-7.47(2H, m), 7.58-7.62(2H, m), 8.01(1H, s) 175 δ 1.22(3H, t, J=7.6Hz), 1.31(6H, d, J=6.3Hz), 2.34(3H, s), 2.69(2H, q, J=7.6Hz), 5.03(1H, septet, J=6.3Hz), 6.70(1H, s), 7.37(2H, s), 7.42-7.47(2H, m), 7.58-7.61(2H, m), 8.02(1H, s) 176 δ1.22(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.33(3H, s), 3.17(1H, septet, J=6.8Hz), 5.03(1H, septet, J=6.3Hz), 6.76(1H, s), 7.35(1H, s), 7.41(1H, s), 7.44(1H, t, J=8.1Hz), 7.56-7.62(3H, m), 8.03(1H, s) 177 δ 1.32(6H, d, J=6.1Hz), 2.35(3H, s), 3.85(3H, s), 5.04(1H, septet, J=6.1Hz), 6.67(1H, s), 6.96(1H, s), 7.13(1H, s), 7.44(1H, t, J=8.1Hz), 7.59-7.65(3H, m), 7.96(1H, s) 178 δ 1.30(6H, d, J=6.1Hz), 2.42(3H, s), 5.00(1H, septet, J=6.1Hz), 6.63(1H, s), 7.27-7.41(8H, m), 7.45(1H, s), 7.53(1H, s), 7.58(1H, d, J=7.8Hz), 7.74(1H, s) 179 δ1.31(6H, d, J=6.1Hz), 2.61(3H, d, J=6.3Hz), 5.05(1H, septet, J=6.1Hz), 6.76(1H, br s), 7.45-7.58(3H, m), 7.70(1H, d, J=8.1Hz), 7.96(1H, t, J=1.8Hz), 8.56-8.58(1H, m), 8.70(1H, br s) 180 δ 1.24(3H, t, J=7.6Hz), 1.31(6H, d, J=6.3Hz), 2.75(2H, q, J=7.6Hz), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.42-7.47(2H, m), 7.57-7.67(4H, m), 8.02(1H, s) 181 δ 0.93(3H, t, J=7.3Hz), 1.32(6H, d, J=6.1Hz), 1.63-1.71(2H, m), 2.70(2H, t, J=7.6Hz), 5.04(1H, septet, J=6.1Hz), 6.72(1H, s), 7.44-7.48(2H, m), 7.57-7.63(3H, m), 7.68(1H, s), 8.02(1H, s) 182 δ1.32(6H, d, J=6.4Hz), 3.92(3H, s), 5.06(1H, septet, J=6.4Hz), 6.73(1H, s), 7.46-7.50(1H, m), 7.55-7.60(2H, m), 7.69(1H, d, J=7.8Hz), 7.96(1H, s), 8.48(1H, d, J=1.2Hz), 8.58(1H, s) 183 δ1.31(6H, d, J=6.2Hz), 2.30(3H, s), 2.44(3H, d, J=6.4Hz), 5.01-5.05(1H, m), 6.72(1H, br-s), 7.44-7.48(2H, m), 7.61-7.62(2H, m), 7.78(1H, s), 8.03(1H, br-s) 184 δ 1.32(6H, d, J=6.1Hz), 2.35(3H, s), 2.58(3H, d, J=6.8Hz), 5.01-5.07(1H, m), 6.68(1H, br-s), 7.35(1H, s), 7.46(1H, t, J=7.8Hz), 7.61-7.65(2H, m), 7.72(1H, s), 8.01(1H, s) 185 δ1.31(6H, d, J=6.4Hz), 2.49(3H, s), 4.77(2H, br-s), 5.06(1H, sept, J=6.4Hz), 6.73(1H, br-s), 7.44-7.49(1H, m), 7.55(1H, s), 7.61-7.63(2H, m), 7.81(1H, s), 8.05(1H, br-s) 186 δ1.32(6H, d, J=6.4Hz), 2.61(3H, s), 5.05(1H, septet), 6.73(1H, br-s), 7.44-7.48(2H, m), 7.57-7.64(2H, m), 7.95(1H, br-s), 8.06(1H, br-s) 187 δ 4.84(2H, s), 7.28(1H, br), 7.45(1H, t, J=8.1Hz), 7.59-7.65(4H, m), 7.81(2H, d, J=8.5Hz), 7.99(1H, s), 8.17(1H, s) 188 δ 2.53(3H, d, J=8.8Hz), 4.85(2H, s), 7.15(1H, br s), 7.45-7.65(6H, m), 8.00-8.02(2H, m) 189 δ 1.34(3H, t, J=7.6Hz), 2.75(2H, q, J=7.6Hz), 4.85(2H, s), 7.10(1H, s), 7.47-7.52(3H, m), 7.59-7.66(2H, m), 7.87(1H, s), 8.05(1H, s), 8.27(1H, d, J=8.8Hz) 190 δ 1.02(3H, t, J=7.3Hz), 1.67-1.77(2H, m), 2.70(2H, t, J=7.6Hz), 4.85(2H, s), 7.10(1H, br-s), 7.44-7.52(3H, m), 7.59-7.65(2H, m), 7.88(1H, s), 8.07(1H, s), 8.30(1H, d, J=8.5Hz) 191 δ3.89(3H, s), 4.85(2H, s), 7.06(1H, dd, J=8.5Hz, 2.0Hz), 7.18(1H, br s), 7.46-7.54(2H, m), 7.61-7.63(2H, m), 7.79-7.80(1H, m), 8.01(1H, s), 8.10(1H, s) 192 δ4.86(2H, s), 7.09(1H, br.), 7.43-7.79(5H, m), 8.03(1H, br.), 8.56(1H, br), 8.76(1H, d, J=8.8Hz) 193 δ4.86(2H, s), 7.16(1H, br s), 7.47-7.74(5H, m), 7.93(1H, s), 8.02(1H, s), 8.23(1H, s) 194 δ 2.30(3H, s), 2.47(3H, d, J=6.0Hz), 4.85(2H, s), 7.12(1H, br- s), 7.42(1H, d, J=9.0Hz), 7.49(1H, t, J=8.1Hz), 7.62-7.67(2H, m), 7.78-7.81(2H, m), 8.03(1H, br-s) 195 δ 2.35(3H, s), 2.52(3H, d, J=8.8Hz), 4.86(2H, s), 7.05(1H, br- s), 7.31(1H, s), 7.50(1H, t, J=7.8Hz), 7.60-7.67(2H, m), 7.71(1H, s), 8.03(1H, s), 8.07(1H, s) 196 δ 1.23(6H, t, J=7.6Hz), 2.70(4H, q, J=7.6Hz), 4.85(2H, s), 7.03(1H, br), 7.39(3H, s), 7.50(1H, t, J=8.1Hz), 7.65(1H, d, J=8.1Hz), 7.69(1H, br-s), 8.04(1H, s) 197 δ 1.23(3H, t, J=7.6Hz), 2.35(3H, s), 2.69(2H, q, J=7.6Hz), 4.85(2H, s), 7.05(1H, br), 7.37(2H, s), 7.42(1H, s), 7.50(1H, t, J=7.8Hz), 7.64-7.66(2H, m), 8.04(1H, s) 198 δ1.23(6H, d, J=6.8Hz), 2.34(3H, s), 3.17(1H, septet, J=6.8Hz), 4.85(2H, s), 7.18(1H, br-s), 7.36(1H, s), 7.42(1H, s), 7.49(1H, t, J=8.1Hz), 7.55(1H, s), 7.65-7.67(2H, m), 8.05(1H, s) 199 δ 2.36(3H, s), 3.86(3H, s), 4.85(2H, s), 6.96(1H, s), 7.01(1H, br), 7.14(1H, s), 7.49(1H, t, J=8.1Hz), 7.64-7.68(3H, m), 7.99(1H, s) 200 δ 2.43(3H, s), 4.83(2H, s), 6.99(1H, br), 7.33-7.42(8H, m), 7.45(1H, s), 7.54(1H, S), 7.64(1H, d, J=6.3Hz), 7.78(1H, s) 201 δ 2.47(3H, s), 4.86(2H, s), 7.06(1H, s), 7.11(1H, br.), 7.24-7.27(1H, m), 7.53(1H, t, J=7.3Hz), 7.66(2H, t, J=7.3Hz), 7.95(1H, s), 8.17(1H, s), 8.85(1H, s) 202 δ1.57(3H, s), 4.86(2H, s), 7.10(1H, br s), 7.52(2H, t, J=7.8Hz), 7.63-7.65(1H, m), 7.72-7.74(1H, m), 8.03(1H, br-s), 8.57-8.59(1H, m), 8.70(1H, br s) 203 δ 2.10(3H, s), 4.84(2H, s), 7.11(1H, d, J=8.8Hz), 7.18-7.22(2H, m), 7.47(1H, t, J=7.8Hz), 7.61(1H, d, J=7.8Hz), 7.65(1H, d, J=7.8Hz), 7.80(1H, br-s), 8.00(1H, br-s) 204 δ1.50(9H, s), 2.29(3H, s), 4.85(2H, s), 6.46(1H, br-s), 7.20(1H, br-s), 7.45-7.49(2H, m), 7.50(1H, d, J=7.3Hz), 7.65(1H, d, J=7.3Hz), 7.88(1H, br-s), 7.99(1H, br-s), 8.19(1H, d, J=8.8Hz) 205 δ 1.26(3H, t, J=7.6Hz), 2.76(2H, q, J=7.6Hz), 4.85(2H, s), 7.06(1H, br), 7.47-7.53(2H, m), 7.58-7.61(2H, m), 7.67-7.69(2H, m), 8.05(1H, s) 206 δ 1.25(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz), 4.85(2H, s), 7.06(1H, br), 7.49-7.53(2H, m), 7.62(1H, s), 7.68-7.70(2H, m), 7.74(1H, s), 8.06(1H, s) 207 δ 1.24(3H, t, J=7.3Hz), 2.77(2H, q, J=7.3Hz), 4.86(2H, s), 7.07(1H, br), 7.50-7.58(3H, m), 7.70-7.72(2H, m), 7.96(1H, s), 8.07(1H, s) 208 δ 0.93(3H, t, J=7.3Hz), 1.63-1.69(2H, m), 2.70(2H, t, J=7.6Hz), 4.85(2H, s), 7.10(1H, s), 7.45(1H, s), 7.49-7.52(1H, m), 7.53(1H, s), 7.58-7.69(3H, m), 8.04(1H, s) 209 δ 0.93(3H, t, J=7.3Hz), 1.61-1.70(2H, m), 2.71(2H, t, J=7.3Hz), 4.85(2H, s), 7.10(1H, br-s), 7.48-7.53(2H, m), 7.63(1H, s), 7.67-7.70(2H, m), 7.74(1H, d, J=2.0Hz), 8.05(1H, s) 210 δ 0.90(3H, t, J=7.3Hz), 1.28-1.38(2H, m), 1.56-1.64(2H, m), 2.73(2H, t, J=7.8Hz), 4.85(2H, s), 7.06(1H, br-s), 7.49-7.53(2H, m), 7.60(1H, s), 7.67-7.74(3H, m), 8.04(1H, s) 211 δ3.93(3H, s), 4.86(2H, s), 7.13(1H, br s), 7.53(1H, t, J=8Hz), 7.61-7.65(2H, m), 7.71(1H, d, J=8Hz), 8.04(1H, s), 8.48(1H, d, J=1.2Hz), 8.58(1H, s) 212 δ 2.47(3H, s), 4.85(2H, s), 7.08(1H, br-s), 7.40(1H, s), 7.51(1H, t, J=7.8Hz), 7.63(1H, s), 7.67-7.71(3H, m), 8.03(1H, s) 213 δ4.86(2H, s), 7.06(1H, br.), 7.52(1H, t, J=7.8Hz), 7.67-7.71(3H, m), 7.67(2H, s), 8.05(1H, s) 214 δ 2.26(3H, s), 2.45(3H, d, J=6.4Hz), 4.86(2H, s), 7.08(1H, br- s), 7.49-7.53(2H, m), 7.69-7.75(3H, m), 8.05(1H, br-s) 215 δ 2.35(3H, s), 2.58(3H, d, J=6.6Hz), 4.85(2H, s), 7.08(1H, br- s), 7.35(1H, s), 7.51(1H, t, J=8.1Hz), 7.68(2H, d, J=8.1Hz), 7.73(1H, s), 8.04(1H, s) 216 δ 2.50(3H, s), 4.77(2H, br-s), 4.86(2H, s), 7.12(1H, br-s), 7.51-7.56(2H, m), 7.69(2H, d, J=7.3Hz), 8.84(1H, s), 8.08(1H, br-s) 217 δ 2.43(3H, s), 4.86(2H, s), 7.12(1H, br-s), 7.51(1H, t, J=7.9Hz), 7.57(1H, br-s), 7.69(1H, d, J=7.9Hz), 7.76(1H, br-s), 7.86(1H, br-s), 8.08(1H, br-s) 218 δ 2.51(3H, s), 4.86(2H, s), 7.00(1H, br-s), 7.50-7.55(2H, m), 7.68-7.70(2H, m), 7.87(1H, br-s), 8.08(1H, br-s) 219 δ 2.62(3H, s), 4.86(2H, s), 7.00(1H, br-s), 7.47(1H, s), 7.52(1H, t, J=7.8Hz), 7.68-7.70(2H, m), 7.89(1H, br-s), 8.07(1H, br- s) 220 δ 2.12(3H, s), 4.50(2H, br-s), 4.86(2H, s), 7.14(1H, br-s), 7.29(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.68-7.70(2H, m), 7.77(1H, br- s), 8.04(1H, br-s) 221 δ 0.90(3H, t, J=7.3Hz), 1.28-1.37(2H, m), 1.55-1.63(2H, m), 2.48-2.60(2H, m), 2.73(2H, t, J=7.8Hz), 4.43(2H, t, J=6.3Hz), 6.85(1H, s), 7.46-7.50(2H, m), 7.60-7.68(3H, m), 7.73(1H, d, J=1.5Hz), 8.00(1H, s) 222 δ1.32(6H, d, J=6.3Hz), 2.39(3H, s), 5.04(1H, septet, J=6.3Hz), 6.71(1H, s), 7.43-7.47(2H, m), 7.57-7.64(3H, m), 7.73(1H, s), 8.04(1H, s) 223 δ 1.32(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H, t, J=8.1Hz), 7.63-7.68(1H, m), 7.67(2H, s), 7.75(1H, d, J=7.6Hz), 8.00(1H, s), 8.06(1H, t, J=1.7Hz), 8.93(1H, s) 224 (DMSO-d₆)δ 1.31(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 7.41(1H, t, J=8.1Hz), 7.64(1H, d, J=8.1Hz), 7.79(1H, d, J=8.1Hz), 7.93(1H, s), 8.00(1H, s), 8.15(1H, 5), 8.26(1H, s), 9.36(1H, s) 225 δ 1.31(6H, d, J=6.3Hz), 2.34(6H, s), 5.03(1H, septet, J=6.3Hz), 6.73(1H, s), 7.33(2H, s), 7.44(1H, t, J=7.8Hz), 7.53-7.62(3H, m), 8.05(1H, s) 226 δ 1.31(6H, d, J=6.3Hz), 2.33(6H, s), 5.02(1H, septet, J=6.3Hz), 6.75(1H, s), 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.52-7.61(3H, m), 8.04(1H, s) 227 δ 4.84(2H, s), 7.24(1H, s), 7.45(1H, t, J=7.8Hz), 7.59-7.62(4H, m), 7.77(2H, d, J=8.8Hz), 7.99(1H, s), 8.16(1H, s) 228 δ 2.39(3H, s), 4.85(2H, s), 7.11(1H, br-s), 7.47-7.52(2H, m), 7.58(1H, s), 7.67-7.70(2H, m), 7.73(1H, s), 8.06(1H, s) 229 (DMSO-d₆)δ 4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.72(1H, s), 7.73(1H, d, J=7.8Hz), 7.83-7.84(2H, m), 8.14(1H, s), 9.27(1H, s), 9.34(1H, s) 230 (DMSO-d₆)δ 4.86(2H, s), 7.44(1H, t, J=8.1Hz), 7.67(1H, s), 7.68(1H, s), 7.71-7.74(1H, m), 7.85(1H, d, J=7.3Hz), 8.15(1H, s), 9.31(1H, s), 9.41(1H, br-s) 231 (DMSO-d₆)δ 4.96(2H, s), 7.51(1H, t, J=7.8Hz), 7.65-7.73(2H, m), 8.13(1H, s), 8.15(1H, s), 8.49(1H, s), 10.41(1H, s), 10.58(1H, s) 232 (DMSO-d₆)δ 4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.88(1H, d, J=7.8Hz), 7.94(1H, s), 8.08(1H, s), 8.16(1H, s), 9.33(1H, s), 9.42(1H, s) 233 δ 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.34(2H, s), 7.47-7.51(2H, m), 7.65-7.68(2H, m), 8.06(1H, s) 234 δ 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.35(2H, s), 7.47-7.52(2H, m), 7.65-7.68(2H, m), 8.05(1H, s) 235 δ 4.84(2H, s), 7.17(1H, br-s), 7.49(1H, t, J=7.8Hz), 7.63(1H, d, J=7.8Hz), 7.67(1H, d, J=7.8Hz), 7.94(1H, s), 8.07(1H, s) 236 δ 4.85(2H, s), 7.14(1H, s), 7.51(1H, t, J=7.8Hz), 7.68-7.73(2H, m), 7.83(1H, s), 7.86(2H, s), 8.07(1H, s) 237 δ 2.48-2.60(2H, m), 4.43(2H, t, J=6.3Hz), 6.90(1H, s), 7.48(1H, t, J=7.8Hz), 7.63-7.69(2H, m), 7.86(3H, s), 8.03(1H, s) 238 (DMSO-d₆)δ 2.50-2.61(2H, m), 4.41(2H, t, J=6.3Hz), 7.43(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.71(1H, s), 7.80-7.84(2H, m), 8.06(1H, s), 8.82(1H, s), 9.26(1H, s) 239 δ 1.34(3H, t, J=7.3Hz), 4.26(2H, q, J=7.3Hz), 6.77(1H, br-s), 7.46-7.53(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-7.94(3H, m), 8.39(1H, s), 8.71(1H, d, J=8.8Hz) 240 δ 1.32(6H, d, J=6.3Hz), 5.06(1H, septet, J=6.3Hz), 6.74(1H, s), 7.45-7.52(2H, m), 7.70(1H, d, J=7.3Hz), 7.86-7.94(3H, m), 8.40(1H, s), 8.71(1H, d, J=8.8Hz) 241 δ 4.58(1H, dd, J=2.0Hz, 5.8Hz), 4.85(1H, dd, J=2.0Hz, 4.2Hz), 7.06(1H, br-s), 7.30(1H, d, J=6.4Hz), 7.49-7.57(2H, m), 7.74(1H, d, J=7.8Hz), 7.87(1H, d, J=7.8Hz), 7.91(1H, s), 7.99(1H, s), 8.40(1H, s), 8.71(1H, d, J=8.8Hz) 242 δ1.62-1.70(2H, m), 1.71-1.87(4H, m), 1.89-1.96(2H, m), 5.22-5.26(1H, m), 6.72(1H, s), 7.45-7.51(2H, m), 7.70(1H, brd, J=7.3Hz), 7.86-7.93(3H, m), 8.34(1H, s), 8.70(1H, d, J=8.8Hz) 243 δ 3.76(2H, t, J=5.4Hz), 4.47(2H, t, J=5.4Hz), 6.97(1H, br-s), 7.47-7.56(2H, m), 7.69(1H, d, J=7.8Hz), 7.86-7.91(2H, m), 7.97(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.8Hz) 244 δ 2.82(2H, t, J=6.3Hz), 4.41(2H, t, J=6.3Hz), 7.46(1H, t, J=7.8Hz), 7.54-7.57(1H, m), 7.81(1H, d, J=8.3Hz), 7.88(1H, d, J=8.8Hz), 7.91(1H, s), 8.10(1H, s), 8.56-8.63(2H, m), 9.55(1H, br-s) 245 δ4.40(2H, dt, J=3.9Hz, 14.1Hz), 6.04(1H, tt, J=3.9Hz, 55.3Hz), 7.43-7.48(1H, m), 7.55(1H, d, J=7.8Hz), 7.80(1H, d, J=7.3Hz), 7.86(1H, d, J=8.8Hz), 7.91(1H, s), 8.07(1H, s), 8.53(1H, s), 8.64(1H, d, J=8.8Hz), 9.42(1H, s) 246 δ4.56(2H, d, J=5.9Hz), 5.92(1H, t, J=5.9Hz), 6.97(1H, br-s), 7.49-7.57(2H, m), 7.69(1H, d, J=7.3Hz), 7.87-7.92(2H, m), 7.98(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.8Hz) 247 δ 4.86(2H, s), 7.15(1H, br-s), 7.50-7.59(2H, m), 7.72(1H, d, J=7.8Hz), 7.86-7.92(2H, m), 8.02(1H, s), 8.40(1H, s), 8.71(1H, d, J=8.8Hz) 248 δ5.05(2H, s), 7.09(1H, br-s), 7.51-7.59(2H, m), 7.73(1H, d, J=7.8Hz), 7.88(1H, d, J=8.3Hz), 7.92(1H, s), 8.03(1H, s), 8.39(1H, s), 8.72(1H, d, J=8.8Hz) 249 δ 2.49-2.60(2H, m), 4.44(2H, t, J=6.3Hz), 6.86(1H, br-s), 7.48-7.56(2H, m), 7.69(1H, d, J=6.3Hz), 7.88(1H, d, J=8.8Hz), 7.92(1H, s), 7.96(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.8Hz) 250 δ4.68(2H, t, J=13.2Hz), 708(1H, br-s), 7.50-7.59(2H, m), 7.70(1H, br-d, J=7.3Hz), 7.87-7.92(2H, m), 8.00(1H, s), 8.39(1H, s), 8.71(1H, d, J=8.7Hz) 251 δ5.29(2H, s), 6.92(1H, br-s), 7.47-7.55(4H, m), 7.65-7.70(3H, m), 7.87(1H, d, J=8.8Hz), 7.92(1H, s), 7.97(1H, s), 8.38(1H, br-s), 8.71(1H, d, J=8.8Hz) 252 δ5.23(2H, s), 6.82(1H, br-s), 7.37(1H, d, J=8.3Hz), 7.50-7.53(2H, m), 7.6(1H, m), 7.75(1H, dd, J=2.4Hz, 8.3Hz), 7.87-7.96(3H, m), 8.38(1H, br-s), 8.47(1H, d, J=2.4Hz), 8.72(1H, d, J=8.3Hz) 253 δ 1.31(6H, d, J=6.3Hz), 2.33(6H, s), 5.02(1H, septet, J=6.3Hz), 6.75(1H, br-s), 7.33(2H, s), 7.43(1H, t, J=7.8Hz), 7.54-7.61(3H, m), 8.04(1H, s) 254 δ 2.34(6H, s), 4.39(2H, dt, J=3.9Hz, 13.6Hz), 6.01(1H, tt, J=3.9Hz, 54.6Hz), 6.98(1H, s), 7.34(2H, s), 7.46-7.50(2H, m), 7.60-7.66(2H, m), 8.02(1H, s) 255 δ 2.34(6H, s), 4.61-4.66(2H, m), 4.71-4.77(2H, m), 5.18-5.30(1H, m), 7.12(1H, s), 7.34(2H, s), 7.45-7.50(1H, m), 7.52-7.66(2H, m), 7.76-7.84(1H, m), 8.04(1H, s) 256 δ 2.34(6H, s), 4.58(2H, q, J=8.3Hz), 7.02(1H, s), 7.34(2H, s), 7.45-7.51(2H, m), 7.62-7.67(2H, m), 8.02(1H, s) 257 δ 2.34(6H, s), 4.85(2H, s), 7.10(1H, br), 7.34(2H, s), 7.47-7.51(2H, m), 7.63-7.67(2H, m), 8.05(1H, s) 258 δ1.48(3H, d, J=6.8Hz), 2.34(6H, s), 5.30-5.36(1H, m), 6.95(1H, br- s), 7.30(2H, s), 7.46-7.51(2H, m), 7.60-7.67(2H, m), 8.03(1H, br-s) 259 δ 2.35(6H, s), 2.49-2.59(2H, m), 4.42(2H, t, J=6.3Hz), 6.85(1H, br- s), 7.34(2H, s), 7.45-7.49(2H, m), 7.60-7.65(2H, m), 8.02(1H, br-s) 300 δ 4.85(2H, s), 7.10(1H, br), 7.50(1H, t, J=7.8Hz), 7.68-7.71(3H, m), 7.72(2H, s), 8.04(1H, s) 301 δ 4.85(2H, s), 7.08(1H, br), 7.51-7.55(1H, m), 7.69-7.72(2H, m), 7.84(1H, s), 8.06(2H, s), 8.10(1H, s) 331 δ 2.29(6H, s), 4.85(2H, s), 7.11-7.19(3H, m), 7.39(1H, s), 7.49(1H, t, J=7.9Hz), 7.66-7.73(2H, m), 8.00(1H, s) 348 δ 2.35(6H, s), 3.81(3H, s), 6.80(1H, br), 7.36(2H, s), 7.44-7.63(4H, m), 8.02(1H, s) 377 δ 2.36(6H, s), 4.85(2H, s), 7.09(1H, s), 7.37(2H, s), 7.44(1H, s), 7.50(1H, t, J=8.3Hz), 7.67(2H, d, J=7.3Hz), 8.05(1H, s) 424 δ4.85(2H, s), 7.10(1H, s), 7.51(1H, t, J=7.8Hz), 7.69-7.70(3H, m), 7.73(2H, s), 8.05(1H, s) 464 δ 2.47-2.59(2H, m), 4.41(2H, t, J=6.3Hz), 6.96(1H, br-s), 7.46(1H, t, J=7.8Hz), 7.63-7.67(2H, m), 7.83(1H, s), 7.91(2H, s), 8.00(1H, s) 471 δ 4.85(2H, s), 7.13(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.68-7.74(3H, m), 7.92(2H, s), 8.04(1H, s) 511 (DMSO-d₆)δ 2.67-2.78(2H, m), 4.34(2H, t, J=5.9Hz), 7.50(1H, t, J=7.8Hz), 7.68-7.73(2H, m), 8.13(1H, s), 8.52(2H, s), 10.02(1H, s), 10.77(1H, s) 518 (DMSO-d₆)δ 4.96(2H, s), 7.52(1H, t, J=7.8Hz), 7.71-7.75(2H, m), 8.16(1H, s), 8.51(2H, s), 10.42(1H, s), 10.79(1H, s) 565 δ4.86(2H, s), 7.00(1H, br-s), 7.52(1H, t, J=8.3Hz), 7.70-7.73(3H, m), 7.93(2H, s), 8.06(1H, s) 605 δ 2.49-2.60(2H, m), 4.43(2H, t, J=6.3Hz), 6.82(1H, s), 7.49(1H, t, J=7.8Hz), 7.66-7.68(3H, m), 7.94(2H, s), 8.01(1H, s) 612 δ4.86(2H, s), 7.45(1H, t, J=7.8Hz), 7.72(1H, d, J=7.8Hz), 7.94(1H, br-s), 7.93(2H, s), 8.13(1H, s), 9.02(1H, s), 9.17(1H, s) 659 δ4.86(2H, s), 7.06(1H, s), 7.51(1H, t, J=7.8Hz), 7.68-7.71(3H, m), 7.93(2H, s), 8.06(1H, s) 706 δ4.84(2H, s), 7.40(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.67-7.75(2H, m), 8.00(1H, s), 8.09(2H, s), 8.24(1H, s) 770 δ 2.39(3H, s), 4.86(2H, s), 7.00(1H, br-s), 7.48-7.67(5H, m), 7.79(1H, s), 8.04(1H, s), 8.24(1H, d, J=8.8Hz) 800 δ 2.31(6H, s), 4.85(2H, s), 7.11(1H, br-s), 7.43(2H, s), 7.47-7.53(2H, m), 7.66(1H, s), 7.67(1H, s), 8.05(1H, s) 817 δ0.89(3H, t, J=7.3Hz), 1.24-1.37(2H, m), 1.55-1.63(2H, m), 2.47-2.59(2H, m), 2.70(2H, t, J=7.8Hz), 4.42(2H, t, J=5.9Hz), 6.96(1H, br-s), 7.43-7.47(2H, m), 7.57(1H, d, J=1.5Hz), 7.62-7.64(2H, m), 7.74(1H, s), 8.00(1H, s) 818 δ0.86(3H, t, J=7.3Hz), 1.24-1.33(2H, m), 1.49-1.57(2H, m), 2.45-2.56(2H, m), 2.67(2H, t, J=7.8Hz), 4.38(2H, t, J=6.3Hz), 7.15(1H, s), 7.39(1H, t, J=7.8Hz), 7.48(1H, s), 7.62-7.64(2H, m), 7.88(1H, s), 7.93(1H, d, J=2.0Hz), 8.01(1H, s) 819 δ 0.81(3H, t, J=7.3Hz), 1.25(3H, d, J=6.8Hz), 1.53-1.64(2H, m), 2.49-2.60(2H, m), 2.92-3.01(1H, m), 4.43(2H, t, J=5.9Hz), 6.87(1H, br), 7.46-7.51(2H, m), 7.62-7.67(3H, m), 7.74(1H, d, J=1.5Hz), 8.01(1H, s) 820 δ1.32(6H, d, J=6.3Hz), 2.36(3H, s), 5.01-5.07(1H, m), 6.69(1H, s), 7.11-7.13(2H, m), 7.44(1H, t, J=8.3Hz), 7.55-7.59(2H, m), 7.68(1H, br-s), 7.95(1H, d, J=8.3Hz), 7.99(1H, s) 821 δ 1.27(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.96(1H, septet, J=6.8Hz), 5.05(1H, septet, J=6.3Hz), 6.79(1H, s), 7.42-7.52(4H, m), 7.72(1H, d, J=7.8Hz), 7.86(1H, t, J=2.0Hz), 8.14(1H, s), 8.21(1H, d, J=8.3Hz) 822 δ 1.33(6H, d, J=6.6Hz), 5.01-5.09(1H, m), 6.73(1H, s), 7.41-7.52(2H, m), 7.57-7.60(1H, m), 7.65(1H, s), 8.05(1H, s), 8.20(2H, s), 8.35(1H, s) 823 δ 1.32(6H, d, J=6.3Hz), 5.04(1H, septet, J=6.3Hz), 6.70(1H, br-s), 6.98-7.06(1H, m), 7.45(1H, t, J=7.8Hz), 7.53-7.55(1H, m), 7.62(1H, d, J=8.8Hz), 7.94(2H, s), 8.07-8.14(1H, m) 824 δ1.32(6H, d, J=6.1Hz), 2.46(3H, s), 2.54(3H, d, J=15Hz), 5.04(1H, septet, J=6.1Hz), 6.72(1H, s), 7.40-7.44(2H, m), 7.51-7.56(3H, m), 7.94(1H, s), 7.97(1H, s) 825 δ 1.31(6H, d, J=6.3Hz), 2.30(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.20(1H, d, J=2.2Hz), 7.32(1H, d, J=2.2Hz), 7.43(1H, t, J=7.8Hz), 7.59-7.62(3H, m), 8.00(1H, s) 826 δ1.31(6H, d, J=6.3Hz), 2.28(3H, s), 2.31(3H, s), 5.03(1H, septet, J=6.3Hz), 6.71(1H, br-s), 7.01(1H, s), 7.13(1H, s), 7.43(1H, t, J=7.8Hz), 7.61-7.63(3H, m), 7.97(1H, s) 827 δ 1.31(6H, d, J=6.1Hz), 2.25(6H, s), 5.03(1H, septet, J=6.1Hz), 6.70(1H, br- s), 7.26(2H, s), 7.38(1H, br-s), 7.43(1H, t, J=7.8Hz), 7.55-7.61(2H, m), 8.01(1H, s) 828 δ 1.31(6H, d, J=6.3Hz), 2.24(6H, s), 5.02(1H, septet, J=6.3Hz), 6.71(1H, br- s), 7.26(2H, s), 7.39-7.44(2H, m), 7.55-7.60(2H, m), 8.00(1H, s) 829 δ1.31(6H, d, J=6.4Hz), 2.23(6H, s), 5.03(1H, septet, J=6.4Hz), 6.69(1H, br-s), 7.37(1H, br-s), 7.43(1H, t, J=7.8Hz), 7.48(2H, s), 7.55-7.61(2H, m), 8.01(1H, br-s) 830 δ1.32(6H, d, J=6.3Hz), 2.35(6H, s), 5.04(1H, septet, J=6.3Hz), 6.72(1H, s), 7.32-7.36(3H, m), 7.41-7.46(4H, m), 7.56-7.63(4H, m), 8.00(1H, s) 831 δ1.32(6H, d, J=6Hz), 2.30(3H, s), 2.32(6H, s), 5.04(1H, septet, J=6Hz), 6.73(1H, s), 7.08(2H, s), 7.22-7.26(4H, m), 7.43-7.48(2H, m), 7.61-7.63(2H, m), 8.01(1H, s) 832 δ1.32(6H, d, J=6Hz), 2.31(6H, s), 2.42(3H, s), 5.04(1H, septet, J=6Hz), 6.71(1H, s), 7.16(1H, d, J=8Hz), 7.30-7.59(7H, m), 7.62(2H, t, J=8Hz), 8.01(1H, s) 833 δ1.31(6H, d, J=6Hz), 2.33(6H, s), 2.49(3H, s), 5.03(1H, septet, J=6Hz), 6.73(1H, s), 7.12-7.25(2H, m), 7.32(2H, s), 7.42-7.52(4H, m), 7.59-7.63(2H, m), 7.99(1H, s) 834 δ1.32(6H, d, J=6Hz), 2.32(6H, s), 3.80(3H, s), 5.04(1H, septet, J=6Hz), 6.73(1H, s), 6.97(1H, d, J=8Hz), 7.02(1H, t, J=7Hz), 7.27(2H, s), 7.30(2H, d, J=7Hz), 7.34-7.46(2H, m), 7.60-7.63(2H, m), 7.95(1H, s) 835 δ1.32(6H, d, J=7Hz), 2.34(6H, s), 3.87(3H, s), 5.04(1H, septet, J=7Hz), 6.72(1H, s), 6.88-6.91(1H, m), 7.11(1H, t, J=2Hz), 7.16(1H, td, J=8Hz, 1Hz), 7.33-7.37(3H, m), 7.43-7.50(2H, m), 7.59-7.64(2H, m), 8.01(1H, s) 836 δ1.32(6H, d, J=7Hz), 2.33(6H, s), 3.85(3H, s), 5.04(1H, septet, J=7Hz), 6.73(1H, br-s), 6.96(2H, d, J=9Hz), 7.29(2H, s), 7.42-7.52(4H, m), 7.60-7.63(2H, m), 8.00(1H, s) 837 δ1.32(6H, d, J=6Hz), 1.44(3H, t, J=7Hz), 2.33(6H, s), 4.08(2H, q, J=7Hz), 5.04(1H, septet, J=6Hz), 6.72(1H, s), 6.94-6.97(2H, m), 7.29(2H, s), 7.42-7.52(4H, m), 7.61-7.63(2H, m), 7.99(1H, s) 838 δ1.31(6H, d, J=6Hz), 2.34(6H, s), 2.53(3H, s), 5.04(1H, septet, J=6Hz), 6.72(1H, s), 7.31-7.65(10H, m), 8.00(1H, s). 839 δ1.31(6H, d, J=6.3Hz), 2.34(6H, s), 5.04(1H, septet, J=6.3Hz), 6.72(1H, s), 7.12-7.32(5H, m), 7.41-7.48(3H, m), 7.61-7.63(2H, m), 7.99(1H, s) 840 δ1.32(6H, d, J=7Hz), 2.34(6H, s), 5.03(1H, septet, J=7Hz), 6.74(1H, br s), 7.01-7.05(1H, m), 7.28-7.64(9H, m), 8.02(1H, s) 841 δ1.31(6H, d, J=7Hz), 2.34(6H, s), 5.04(1H, septet, J=7Hz), 6.73(1H, s), 7.11(2H, t, J=9Hz), 7.28(2H, s), 7.42-7.63(6H, m), 8.01(1H, s) 842 δ1.24(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.32(3H, s), 2.86(1H, septet, J=6.8Hz), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.08(1H, s), 7.33(1H, d, J=2.0Hz), 7.43(1H, t, J=7.8Hz), 7.61-7.65(3H, m), 7.96(1H, s) 843 δ1.32(6H, d, J=6.3Hz), 2.37(3H, s), 5.03(1H, septet, J=6.3Hz), 6.74(1H, s), 7.46(1H, t, J=7.8Hz), 7.51-7.57(2H, m), 7.61-7.65(2H, m), 7.90(1H, s), 8.08(1H, s) 844 δ 1.32(6H, d, J=6.3Hz), 2.35(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.09(1H, s), 7.21(1H, d, J=2.2Hz), 7.44(1H, t, J=8.1Hz), 7.52-7.61(3H, m), 8.02(1H, s) 845 δ 1.29(6H, d, J=6.8Hz), 1.31(6H, d, J=6.3Hz), 2.98(1H, septet, J=6.8Hz), 5.04(1H, septet, J=6.3Hz), 6.70(1H, s), 7.42-7.48(2H, m), 7.56-7.67(4H, m), 7.92(1H, s) 846 δ 1.32(6H, d, J=6.3Hz), 5.03(1H, septet, J=6.3Hz), 6.75(1H, br-s), 7.41-7.51(2H, m), 7.62-7.65(1H, m), 7.91(1H, br-s), 8.08(1H, s) 847 (DMSO-d₆)δ 1.24-1.44(5H, m), 1.68-1.80(5H, m), 2.46-2.50(1H, m), 4.97(2H, s), 7.19(2H, d, J=8.8Hz), 7.47(1H, t, J=7.8Hz), 7.60-7.70(4H, m), 8.04(1H, s), 10.19(1H, s), 10.37(1H, s) 848 δ 4.84(2H, s), 7.29(1H, d, J=7.8Hz), 7.35(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.56-7.67(3H, m), 7.75(1H, d, J=7.3Hz), 7.97(1H, s), 8.23(1H, s), 8.37(1H, d, J=7.8Hz) 849 δ 4.85(2H, s), 7.12(1H, br-s), 7.47(1H, t, J=7.8Hz), 7.59-7.67(4H, m), 7.72-7.75(2H, m), 7.99(1H, s), 8.03(1H, s) 850 (DMSO-d₆)δ 4.87(2H, s), 7.43(1H, t, J=7.8Hz), 7.65(1H, d, J=7.8Hz), 7.82(1H, d, J=7.8Hz), 7.96(2H, d, J=8.8Hz), 8.07(1H, s), 8.18-8.22(2H, m), 9.66(1H, br), 10.51(1H, s) 851 δ4.85(2H, s), 6.67(1H, br-s), 7.47(1H, t, J=7.8Hz), 7.60-7.64(2H, m), 7.65(2H, d, J=8.8Hz), 7.74(2H, d, J=8.8Hz), 7.98(1H, s), 8.00(1H, s) 852 δ4.86(2H, s), 7.09(1H, br-s), 7.48-7.53(1H, m), 7.61-7.65(2H, m), 7.81(2H, d, J=8.8Hz), 7.95(2H, d, J=8.8Hz), 7.95-8.04(1H, m), 8.14(1H, s) 854 δ0.90(3H, t, J=7.3Hz), 1.28-1.38(2H, m), 1.56-1.65(2H, m), 2.72(2H, t, J=7.8Hz), 4.85(2H, s), 7.14(1H, br-s), 7.45(1H, s), 7.50(1H, t, J=7.8Hz), 7.58(1H, d, J=1.5Hz), 7.66-7.68(3H, m), 8.04(1H, s) 855 δ 0.88(3H, t, J=7.3Hz), 1.24-1.35(2H, m), 1.52-1.60(2H, m), 2.70(2H, t, J=7.8Hz), 4.84(2H, s), 7.27(1H, s), 7.46-7.50(2H, m), 7.67-7.69(2H, m), 7.76(1H, s), 7.94(1H, d, J=1.5Hz), 8.06(1H, s) 856 δ 0.81(3H, t, J=7.3Hz), 1.25(3H, d, J=5.9Hz), 1.55-1.65(2H, m), 2.91-3.01(1H, m), 4.85(2H, s), 7.14(1H, br), 7.50-7.53(2H, m), 7.61-7.77(4H, m), 8.05(1H, s) 857 δ0.90(3H, t, J=7.3Hz), 1.31(3H, d, J=6.8Hz), 1.63-1.74(2H, m), 2.82-2.91(1H, m), 4.85(2H, s), 7.22(1H, s), 7.47-7.53(3H, m), 7.58-7.62(1H, m), 7.66(1H, d, J=8.3Hz), 7.93(1H, s), 8.05(1H, s), 8.13-8.15(1H, m) 858 δ 2.36(3H, s), 4.85(2H, s), 7.11-7.14(3H, m), 7.49(1H, t, J=8.3Hz), 7.61-7.69(3H, m), 7.95(1H, d, J=8.3Hz), 8.02(1H, s) 859 δ 2.31(3H, s), 4.34(2H, q, J=7.8Hz), 4.84(2H, s), 6.80-6.86(2H, m), 7.16(1H, br-s), 7.47(1H, t, J=7.8Hz), 7.60-7.72(4H, m), 7.99(1H, br-s) 860 δ 2.39(3H, s), 4.85(2H, s), 7.09-8.14(9H, m) 861 δ 2.31(3H, s), 4.84(2H, s), 7.17(1H, br), 7.20-7.23(2H, m), 7.47(1H, t, J=8.1), 7.58-7.67(3H, m), 7.84-7.87(1H, m), 8.00(1H, s) 862 δ 1.27(6H, d, J=6.8Hz), 2.97(1H, septet, J=6.8Hz), 4.85(2H, s), 7.18(1H, br), 7.46-7.51(3H, m), 7.57(1H, dd, J=1.5Hz, 7.8Hz), 7.74(1H, d, J=7.8Hz), 7.94(1H, s), 8.14(1H, s), 8.21(1H, d, J=8.3Hz) 863 δ4.87(2H, s), 7.51-8.01(8H, m), 8.86(1H, s) 864 δ 4.87(2H, s), 7.08(1H, br.), 7.49-7.58(4H, m), 8.07(1H, br.), 8.20(3H, s) 865 δ 4.86(2H, s), 7.08(1H, br-s), 7.48-7.60(3H, m), 7.64(1H, d, J=2.4Hz), 7.72(1H, d, J=7.3Hz), 7.98(1H, s), 8.18(1H, s), 8.39(1H, d, J=8.8Hz) 866 δ 4.85(2H, s), 7.06(1H, br), 7.41-7.51(2H, m), 7.60(1H, s), 7.65-7.74(4H, m), 7.97(1H, s) 867 δ4.86(2H, s), 7.10(1H, br-s), 7.48-7.57(2H, m), 7.71(1H, d, J=8.3Hz), 7.90-7.97(3H, m), 8.19(1H, br-s), 8.22(1H, d, J=8.8Hz) 868 δ 4.85(2H, s), 7.12(1H, br-s), 7.46-7.56(4H, m), 7.71(1H, d, J=7.8Hz), 7.99(1H, s), 8.14(1H, s), 8.48(1H, d, J=8.8Hz) 869 δ 4.84(2H, s), 6.97-7.05(1H, m), 7.22(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.59(1H, d, J=7.8Hz), 7.69(1H, d, J=7.8Hz), 7.96(1H, s), 7.98(1H, s), 8.05-8.12(1H, m) 870 δ 2.46(3H, s), 2.55(3H, d, J=14Hz), 4.86(2H, s), 7.13(1H, br s), 7.40(1H, s), 7.46-7.62(4H, m), 7.88(1H, s), 7.99(1H, s) 871 δ 2.34(3H, s), 2.38(3H, s), 4.85(2H, s), 6.97-8.03(8H, m) 872 δ 2.31(6H, s), 3.99(1H, s), 4.85(2H, s), 7.15(1H, br-s), 7.45-7.51(4H, m), 7.64-7.66(2H, m), 8.01(1H, s) 873 δ 2.34(6H, s), 3.74(1H, s), 4.85(2H, s), 7.08(1H, br-s), 7.48(1H, s), 7.49(2H, s), 7.52(1H, s), 7.65-7.67(2H, m), 8.04(1H, s) 874 δ 2.30(6H, s), 4.87(2H, s), 7.08(1H, br), 7.49-7.58(4H, m), 8.07(1H, br), 8.20(3H, s) 875 δ 2.25(6H, s), 4.85(2H, s), 7.07(1H, br), 7.12(2H, s), 7.36(1H, br- s), 7.48(1H, t, J=7.8Hz), 7.64-7.66(2H, m), 8.02(1H, s) 876 δ 2.28(3H, s), 2.31(3H, s), 4.84(2H, s), 7.00(1H, s), 7.12(1H, s), 7.18(1H, br), 7.47(1H, t, J=7.8Hz), 7.60(1H, s), 7.66-7.68(2H, m), 7.99(1H, s) 877 δ 2.19(6H, s), 4.82(2H, s), 7.22(2H, s), 7.41(1H, t, J=8.1Hz), 7.48(1H, br), 7.61-7.66(3H, m), 7.99(1H, s) 878 δ 2.22(6H, s), 4.84(2H, s), 7.13(1H, br-s), 7.39(1H, s), 7.45-7.49(3H, m), 7.64-7.65(2H, m), 8.01(1H, br-s) 879 δ 2.35(6H, s), 4.85(2H, s), 7.09(1H, s), 7.32-7.69(11H, m), 8.02(1H, s) 880 δ 2.30(3H, s), 2.32(6H, s), 4.85(2H, s), 7.09(2H, s), 7.13(1H, s), 7.21-7.27(4H, m), 7.46-7.51(2H, m), 7.68(2H, d, J=7Hz), 8.03(1H, s) 881 δ 2.34(6H, s), 2.42(3H, s), 4.85(2H, s), 7.12-7.23(2H, m), 7.29-7.39(4H, m), 7.47-7.52(2H, m), 7.68(2H, d, J=7Hz), 8.03(1H, s) 882 δ 2.34(6H, s), 2.40(3H, s), 4.85(2H, s), 7.13(1H, d, J=4Hz), 7.23-7.26(2H, m), 7.30(2H, s), 7.33-7.50(4H, m), 7.67(2H, d, J=8Hz), 8.02(1H, s) 883 δ 2.32(6H, s), 3.81(3H, s), 4.85(2H, s), 6.97-7.04(2H, m), 7.10(1H, br s), 7.28(2H, s), 7.30-7.34(2H, m), 7.42(1H, s), 7.49(1H, t, J=8Hz), 7.66-7.70(2H, m), 7.99(1H, s) 884 δ 2.35(6H, s), 3.88(3H, s), 4.85(2H, s), 6.89-6.91(1H, m), 7.10-7.18(3H, m), 7.33-7.37(3H, m), 7.47-7.52(2H, m), 7.68(2H, d, J=7Hz), 8.03(1H, s) 885 δ 2.33(6H, s), 3.86(3H, s), 4.85(2H, s), 6.96(2H, d, J=9Hz), 7.14(1H, br s), 7.30(2H, s), 7.47-7.53(4H, m), 7.68(2H, d, J=7Hz), 8.02(1H, s) 886 δ1.44(3H, t, J=7Hz), 2.33(6H, s), 4.08(2H, q, J=7Hz), 4.85(2H, s), 6.95(2H, d, J=9Hz), 7.13(1H, s), 7.30(2H, s), 7.45-7.52(4H, m), 7.68(2H, d, J=7Hz), 8.01(1H, s) 887 δ 2.33(6H, s), 2.53(3H, s), 4.84(2H, s), 7.14(1H, s), 7.30-7.38(4H, m), 7.46-7.57(4H, m), 7.67(2H, d, J=6Hz), 8.02(1H, s) 888 δ 2.34(6H, s), 4.85(2H, s), 7.10-7.34(6H, m), 7.41-7.52(3H, m), 7.68(2H, d, J=8Hz), 8.02(1H, s) 889 δ 2.34(6H, s), 4.85(2H, s), 7.01-7.06(1H, m), 7.16(1H, br s), 7.25-7.50(8H, m), 7.68(1H, d, J=8Hz), 8.03(1H, s) 890 δ 2.33(6H, s), 4.85(2H, s), 7.09-7.15(3H, m), 7.29(2H, s), 7.46-7.55(4H, m), 7.67-7.69(2H, m), 8.03(1H, s) 891 δ 2.34(6H, s), 4.85(2H, s), 7.09(1H, br s), 7.18-7.30(4H, m), 7.34-7.51(3H, m), 7.67-7.69(2H, m), 8.04(1H, s) 892 δ 2.30(9H, s), 4.85(2H, s), 7.05(1H, t, J=8.8Hz), 7.14(1H, br s), 7.28(2H, s), 7.32-7.51(4H, m), 7.67-7.69(2H, m), 8.03(1H, s) 893 δ 2.31(6H, s), 4.85(2H, s), 6.69(1H, s), 7.09(1H, br-s), 7.25(2H, s), 7.41(1H, s), 7.47-7.51(2H, m), 7.66-7.68(2H, m), 7.72(1H, s), 8.02(1H, s) 894 δ 2.30(6H, s), 4.84(2H, s), 7.07-7.09(1H, m), 7.25(1H), 7.27-7.29(1H, m), 7.36(2H, s), 7.36(2H, s), 7.45-7.50(2H, m), 7.65-7.67(2H, m), 8.02(1H, s) 895 δ 2.32(6H, s), 4.85(2H, s), 7.18(1H, s), 7.35-7.50(7H, m), 7.67(2H, d, J=6.8Hz), 8.02(1H, s) 896 δ 2.31(3H, s), 4.85(2H, s), 7.10(1H, br), 7.20(1H, d, J=2.2Hz), 7.32(1H, d, J=2.2Hz), 7.49(1H, t, J=7.8Hz), 7.57(1H, s), 7.66-7.68(2H, m), 8.02(1H, s) 897 (DMSO-d₆)δ 4.85(2H, s), 7.44(1H, t, J=7.8Hz), 7.63-7.68(2H, m), 7.72(1H, d, J=2.4Hz), 7.84(1H, s), 8.06(1H, s), 8.80(1H, s), 9.09(1H, s) 898 δ4.85(2H, s), 7.00(1H, br-s), 7.51(1H, t, J=8.3Hz), 7.69-7.72(5H, m), 8.05(1H, s) 899 δ4.86(2H, s), 7.00(1H, br-s), 7.53(1H, t, J=7.8Hz), 7.67-7.73(2H, m), 7.92(1H, s), 8.05(2H, s), 8.11(1H, s) 900 (DMSO-d₆)δ 4.98(2H, s), 7.52(1H, t, J=7.8Hz), 7.70-7.75(2H, m), 8.17(1H, s), 8.31(2H, s), 10.42(1H, s), 10.63(1H, s) 901 (DMSO-d₆)δ 1.24-1.47(5H, m), 1.66-1.80(5H, m), 2.54-2.60(1H, m), 4.96(2H, s), 7.48(1H, t, J=7.8Hz), 7.60(2H, s), 7.67-7.71(2H, m), 8.11(1H, s), 10.24(1H, s), 10.37(1H, s) 902 (DMSO-d₆)δ 4.86(2H, s), 7.44(1H, t, J=7.8Hz), 7.67(1H, d, J=7.8Hz), 7.82(1H, d, J=2.0Hz), 7.85(1H, s), 8.05(1H, d, J=2.0Hz), 8.06(1H, d, J=7.8Hz), 9.04(1H, s), 9.27(1H, s) 903 δ4.86(2H, s), 7.00(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.70(2H, d, J=7.8Hz), 7.75(1H, s), 7.94(2H, s), 8.06(1H, s) 904 δ 2.20(3H, s), 4.85(2H, s), 6.60(1H, d, J=2.4Hz), 7.17(1H, br.), 7.50(1H, t, J=7.8Hz), 7.54(1H, s), 7.59(1H, s), 7.69(1H, d, J=7.8Hz), 7.72(1H, br), 8.03(1H, s) 905 δ 2.36(3H, s), 4.85(2H, s), 7.08(1H, br-s), 7.10(1H, s), 7.22-7.23(1H, m), 7.50(1H, t, J=8.1Hz), 7.59(1H, s), 7.67-7.69(2H, m), 8.04(1H, s) 906 δ 2.36(3H, s), 4.86(2H, s), 4.88(2H, s), 7.04(1H, br.), 7.12(1H, d, J=2.4Hz), 7.27(1H, s), 7.50(1H, t, J=7.8Hz), 7.56(1H, s), 7.67-7.70(2H, m), 8.02(1H, s) 907 δ 2.38(3H, s), 4.85(2H, s), 7.14(1H, br), 7.49-7.53(2H, m), 7.62-7.70(3H, m), 7.85(1H, s), 8.09(1H, s) 908 δ 2.28(3H, s), 4.84(2H, s), 7.11(1H, br-s), 7.48(1H, t, J=7.8Hz), 7.55(1H, s), 7.59(1H, s), 7.64-7.68(3H, m), 8.01(1H, br-s) 909 δ1.24(6H, d, J=6.8Hz), 2.33(3H, s), 2.86(1H, septet, J=6.8Hz), 4.85(2H, s), 7.09(1H, s), 7.16(1H, br), 7.33(1H, d, J=2.0Hz), 7.48(1H, t, J=7.8Hz), 7.60(1H, s), 7.67-7.69(2H, m), 8.00(1H, s) 910 δ 2.23(3H, s), 4.86(2H, s), 6.51(1H, s), 6.78(1H, d, J=2.4Hz), 7.15(1H, br.), 7.49(1H, br.), 7.51(1H, t, J=7.8), 7.56(1H, s), 7.71(1H, d, J=6.8Hz), 8.05(1H, s) 911 δ 1.29(6H, d, J=7.3Hz), 2.98(1H, septet, J=7.3Hz), 4.85(2H, s), 7.10(1H, br), 7.47-7.52(2H, m), 7.56-7.58(2H, m), 7.65(1H, d, J=7.3Hz), 7.72(1H, br), 7.96(1H, s) 912 δ 2.37(3H, s), 4.85(2H, s), 4.88(2H, s), 7.06(1H, br), 7.16(1H, d, J=2.4Hz), 7.43(1H, d, J=2.4Hz), 7.50(1H, t, =7.8Hz), 7.56(1H, s), 7.68(1H, s), 7.70(1H, s), 8.03(1H, s) 913 (DMSO-d₆)δ 4.96(2H, s), 7.49(1H, t, J=7.8Hz), 7.64(1H, d, J=7.8Hz), 7.71(1H, d, J=7.8Hz), 8.02(1H, d, J=2.0Hz), 8.10(1H, s), 8.30(1H, d, J=2.0Hz), 10.34(1H, s), 10.38(1H, s) 914 (DMSO-d₆)δ 1.29(6H, d, J=6.8Hz), 2.99(1H, septet, J=6.8Hz), 4.86(2H, s), 7.42(1H, t, J=7.8Hz), 7.52(1H, d, J=1.5Hz), 7.68(1H, d, J=7.8Hz), 7.74(1H, d, J=1.5Hz), 7.85(1H, d, J=7.8Hz), 8.09(1H, s), 9.27(1H, s), 9.66(1H, s) 915 δ 4.85(2H, s), 7.04(1H, br), 7.47-7.55(2H, m), 7.63-7.70(3H, m), 7.90(1H, d, J=1.5Hz), 7.99(1H, s) 916 (DMSO-d6)δ 4.86(2H, s), 7.43(1H, t, J=7.8Hz), 7.70(1H, d, J=7.8Hz), 7.84(1H, d, J=7.8Hz), 8.10(1H, s), 9.46(1H, br-s), 9.73(1H, br-s) 917 δ 2.22(6H, s), 3.79(2H, t, J=5.4Hz), 4.42(2H, t, J=5.4Hz), 7.37(1H, t, J=7.8Hz), 7.44(2H, s), 7.63(1H, d, J=7.8Hz), 7.71(1H, d, J=7.8Hz), 8.12(1H, br-s), 9.37(1H, s), 9.60(1H, br-s) 918 δ 2.34(6H, s), 2.53-2.56(2H, m), 4.43(2H, t, J=6.3Hz), 6.80(1H, br-s), 7.41(1H, s), 7.47(2H, s), 7.50(1H, s), 7.62-7.64(2H, m), 7.9(1H, s) 919 (DMSO-d₆)δ 2.66-2.78(2H, m), 4.34(2H, t, J=5.9Hz), 7.49(1H, t, J=7.8Hz), 7.66-7.72(2H, m), 8.12(1H, s), 8.30(2H, s), 10.00(1H, s), 10.60(1H, s) 920 δ 1.32(6H, d, J=6.1Hz), 2.51(3H, s), 5.01-5.07(1H, m), 6.72(1H, br-s), 7.50(1H, t, J=7.8Hz), 7.54-7.57(2H, m), 7.64(1H, d, J=8.1Hz), 7.71(2H, d, J=7.3Hz), 7.85(1H, s), 8.01-8.03(1H, m), 8.13(1H, s), 8.45-8.48(1H, m) 921 δ1.32(6H, d, J=6.1Hz), 1.74-1.77(2H, m), 1.84-1.87(2H, m), 2.74(2H, t, J=6.4Hz), 3.02(2H, q, J=6.4Hz), 5.04(1H, septet, J=6.1Hz), 6.73(1H, br s), 7.42-7.46(2H, m), 7.52-7.55(1H, m), 7.62(1H, br s, J=8Hz), 7.76(1H, br s), 7.96(1H, br s), 8.03-8.06(1H, m) 922 δ1.31(6H, d, J=6.4Hz), 1.68-1.76(4H, m), 2.81(2H, t, J=5.7Hz), 2.99(2H, q, J=6.1Hz), 5.03(1H, septet, J=6.4Hz), 6.73(1H, br-s), 7.43-7.47(2H, m), 7.59-7.64(3H, m), 8.03(1H, s) 923 δ1.31(6H, d, J=6.4Hz), 3.83(3H, s), 5.02(1H, septet, J=6.4Hz), 6.55(1H, s), 6.78(1H, br-s), 7.41-7.50(2H, m), 7.57(1H, d, J=7.8Hz), 8.03(1H, br-s), 8.08(1H, br- s) 924 δ1.32(6H, d, J=6.3Hz), 3.86(3H, s), 5.04(1H, septet, J=6.3Hz), 6.72(1H, br-s), 7.45-7.53(2H, m), 7.63(1H, d, J=7.3Hz), 7.80(1H, br-s), 8.14(1H, br-s) 925 δ1.32(6H, d, J=5.9Hz), 3.89(3H, s), 5.04(1H, septet, J=5.9Hz), 6.72(1H, s), 7.47-7.50(2H, m), 7.70(1H, d, J=8.3Hz), 7.90(1H, br-s), 8.14(1H, br-s) 926 δ1.32(6H, d, J=6.1Hz), 3.88(3H, s), 3.93(3H, s), 5.04(1H, septet), 6.78(1H, br- s), 7.47(1H, br-s), 7.64-7.68(2H, m), 8.05(1H, br-s), 9.40(1H, br-s) 927 δ1.33(6H, d, J=5.9Hz), 2.34(3H, s), 5.02(1H, septet, J=5.9Hz), 6.74(1H, br-s), 7.24(1H, s), 7.44(1H, t, J=7.8Hz), 7.49-7.52(1H, m), 7.58-7.60(1H, m), 7.82(1H, br-s), 8.07(1H, br-s), 8.71(1H, s) 928 δ1.31(6H, d, J=6.4Hz), 2.35(3H, s), 5.01-5.07(1H, m), 6.74(1H, br-s), 7.25(1H, s), 7.46(1H, t, J=7.8Hz), 7.58-7.63(2H, m), 7.68(1H, br-s), 8.07(1H, br-s) 929 δ1.32(6H, d, J=5.9Hz), 5.03(1H, septet, J=5.9Hz), 6.52(1H, septet, J=6.3Hz), 6.71(1H, br-s), 6.99(1H, d, J=8.8Hz), 7.43(1H, t, J=7.8Hz), 7.51-7.58(2H, m), 7.92(1H, br-s), 8.01(1H, br-s), 8.14(1H, dd, J=8.8Hz, 2.4Hz), 8.34(1H, d, J=2.4Hz) 930 δ1.32(6H, d, J=5.9Hz), 2.33(3H, s), 5.50(1H, septet, J=5.9Hz), 6.53(1H, septet, J=6.4Hz), 6.74(1H, br-s), 6.87(1H, s), 7.43(1H, t, J=7.8Hz), 7.54-7.58(2H, m), 7.64(1H, br-s), 8.04(1H, br-s), 8.37(1H, s) 931 δ1.32(6H, d, J=6.3Hz), 5.05(1H, septet, J=6.3Hz), 6.30(1H, septet, J=6.3Hz), 6.69(1H, br-s), 7.01(1H, d, J=8.8Hz), 7.47(1H, t, J=7.8Hz), 7.56(1H, dd, J=7.8Hz, 1.5Hz), 7.68(1H, d, J=7.8Hz), 7.98(1H, br-s), 8.27(1H, br-s), 8.82(1H, d, J=8.8Hz) 932 δ1.32(6H, d, J=6.4Hz), 2.29(3H, s), 2.41(3H, s), 5.04(1H, septet, J=6.4Hz), 6.58(1H, septet, J=6.4Hz), 6.72(2H, s), 7.37-7.46(2H, m), 7.53-7.57(1H, m), 7.60(1H, d, J=7.8Hz), 8.05(1H, br-s) 933 δ 2.49(3H, s), 4.85(2H, s), 7.16(1H, br-s), 7.48-7.57(3H, s), 7.70(2H, s), 7.76(1H, d, J=7.6Hz), 7.92(1H, s), 8.00(1H, dd, J=3.4Hz, 6.8Hz), 8.13(1H, s), 8.47(1H, dd, J=3.4Hz, 6.8Hz) 934 δ1.75-1.79(2H, m), 1.84-1.87(2H, m), 2.74(2H, t, J=6.4Hz), 3.02(2H, q, J=6.4Hz), 4.85(2H, s), 7.13(1H, br s), 7.41-7.51(2H, m), 7.59-7.69(2H, m), 7.76(1H, br s), 8.00(1H, br s), 8.06(1H, br d, J=8.5Hz) 935 δ1.65-1.76(4H, m), 2.81(2H, t, J=6.1Hz), 2.99(2H, q, J=6.4Hz), 4.85(2H, s), 7.10(1H, br-s), 7.48-7.52(2H, m), 7.59(1H, s), 7.67-7.69(2H, m), 8.04(1H, s) 936 δ3.86(3H, s), 4.85(2H, s), 6.58(1H, s), 7.10(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.60(1H, d, J=7.8Hz), 7.65(1H, d, J=7.8Hz), 7.84(1H, br-s), 8.10(1H, br-s) 937 δ3.85(3H, s), 4.85(2H, s), 7.16(1H, br-s), 7.51(1H, t, J=7.9Hz), 7.62(1H, d, J=7.9Hz), 7.68(1H, d, J=7.9Hz), 7.85(1H, br-s), 8.12(1H, br-s) 938 δ3.87(3H, s), 4.85(2H, s), 7.21(1H, br-s), 7.51(1H, t, J=8.3Hz), 7.61(1H, d, J=8.3Hz), 7.68(1H, d, J=8.3Hz), 7.92(1H, br-s), 8.13(1H, br-s) 939 δ3.89(3H, s), 3.94(3H, s), 4.86(2H, s), 7.20(1H, br-s), 7.52(1H, t, J=7.8Hz), 7.70-7.73(2H, m), 8.09(1H, br-s), 9.44(1H, s) 940 δ4.87(2H, s), 7.07-7.11(2H, m), 7.31-7.34(1H, m), 7.47-7.52(2H, m), 7.67-7.69(1H, m), 8.01(1H, dd, J=8.0Hz, 1.4Hz), 8.19(1H, br-s), 8.58-8.60(1H, m), 11.3(1H, br-s) 941 δ4.84(2H, s), 7.19(1H, br-s), 7.33(1H, dd, J=8.3Hz, 4.8Hz), 7.44(1H, t, J=8.3Hz), 7.58-7.59(2H, m), 7.94-7.97(2H, m), 8.44(1H, dd, J=4.8Hz, 1.4Hz), 9.14(1H, br-s) 942 δ 2.44(3H, s), 4.86(2H, s), 7.11(1H, br-s), 7.52(1H, t, J=7.8Hz), 7.59(1H, d, J=2.9Hz), 7.63-7.65(2H, m), 7.76(1H, s), 8.09(1H, s), 9.23(1H, s) 943 δ4.85(2H, s), 6.52(1H, septet, J=6.3Hz), 6.99(1H, d, J=8.8Hz), 7.07(1H, br-s), 7.48(1H, t, J=8.3Hz), 7.61-7.62(2H, m), 7.86(1H, s), 8.02(1H, s), 8.15(1H, dd, J=8.8Hz, 2.5Hz), 8.33(1H, d, J=2.5Hz) 944 δ 2.35(3H, s), 4.85(2H, s), 6.55(1H, septet, J=6.4Hz), 6.89(1H, s), 7.08(1H, br-s), 7.49(1H, t, J=7.8Hz), 7.59(1H, s), 7.63(2H, d, J=8.3Hz), 8.05(1H, s), 8.40(1H, s) 945 δ 2.34(3H, s), 4.85(2H, s), 7.17(1H, br-s), 7.22-7.26(1H, m), 7.49(1H, t, J=7.8Hz), 7.60-7.66(2H, m), 7.75(1H, br-s), 8.07(1H, br-s), 8.73(1H, br-s) 946 δ4.86(2H, s), 7.13(1H, br-s), 7.52(1H, t, J=8.3Hz), 7.67(1H, d, J=8.3Hz), 7.74(1H, d, J=8.3Hz), 8.02(1H, s), 8.05(1H, s), 8.66(1H, s), 8.70(1H, br-s) 947 δ 2.36(3H, s), 5.05(2H, s), 7.16(1H, br-s), 7.25(1H, s), 7.51(1H, t, J=7.8Hz), 7.68-7.70(3H, m), 8.08(1H, br-s) 948 δ4.86(2H, s), 6.30(1H, septet, J=6.4Hz), 7.00(1H, d, J=8.8Hz), 7.04(1H, br-s), 7.52(1H, t, J=7.8Hz), 7.63(1H, dd, J=7.8Hz, 1.5Hz), 7.70(1H, d, J=7.8Hz), 8.04(1H, br-s), 8.27(1H, br-s), 8.83(1H, d, J=8.8Hz) 992 δ 2.37(3H, s), 4.85(2H, s), 6.33(1H, septet, J=5.8Hz), 6.87(1H, s), 7.05(1H, br-s), 7.49-7.53(2H, m), 7.66-7.68(2H, m), 8.05(1H, s) 1010 δ1.33(6H, d, J=6.4Hz), 2.37(3H, s), 5.04(1H, septet, J=6.4Hz), 6.34(1H, septet, J=6.4Hz), 6.72(1H, br-s), 6.88(1H, s), 7.45(1H, t, J=7.8Hz), 7.58-7.64(3H, m), 8.05(1H, s) 1039 δ 2.38(3H, s), 4.86(2H, s), 6.34(1H, septet), 6.89(1H, s), 7.09(1H, br-s), 7.51(1H, t, J=7.8Hz), 7.57(1H, br-s), 7.66(1H, br-s), 7.68(1H, d, J=7.8Hz), 8.07(1H, s) 1086 δ 2.37(3H, s), 4.85(2H, s), 6.33(1H, septet, J=5.8Hz), 6.87(1H, s), 7.05(1H, br-s), 7.49-7.53(2H, m), 7.66-7.68(2H, m), 8.05(1H, s) 1104 δ1.32(6H, d, J=6.4Hz), 2.29(3H, s), 2.41(3H, s), 5.04(1H, septet, J=6.4Hz), 6.58(1H, septet, J=6.4Hz), 6.72(2H, s), 7.37-7.46(2H, m), 7.53-7.57(1H, m), 7.60(1H, d, J=7.8Hz), 8.05(1H, br-s) 1180 δ 2.46(3H, s), 4.86(2H, s), 7.11(1H, s), 7.51-7.86(5H, m), 8.10(1H, br-s) 1198 δ 1.31(6H, d, J=6.3Hz), 2.40(3H, s), 5.03(1H, septet, J=6.3Hz), 6.72(1H, s), 7.42-7.47(2H, m), 7.56(1H, s), 7.60-7.63(2H, m), 7.74(1H, s), 8.03(1H, s) 1227 δ 2.41(3H, s), 4.85(2H, s), 7.05(1H, br), 7.44(1H, s), 7.51(1H, t, J=8.1Hz), 7.57(1H, s), 7.67-7.70(3H, m), 8.05(1H, s) 1245 δ 1.31(6H, d, J=6.1Hz), 2.42(3H, s), 5.04(1H, septet, J=6.1Hz), 6.71(1H, s), 7.45(1H, d, J=8.1Hz), 7.48(1H, s), 7.61-7.64(2H, m), 7.72-7.74(2H, m), 8.04(1H, s) 1274 δ 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.48-7.53(2H, m), 7.68-7.73(4H, m), 8.06(1H, s) 1292 δ 1.32(6H, d, J=6.3Hz), 2.42(3H, s), 5.04(1H, septet, J=6.3Hz), 6.72(1H, s), 7.44-7.52(2H, m), 7.62-7.66(3H, m), 7.93(1H, s), 8.04(1H, s) 1321 δ 2.43(3H, s), 4.86(2H, s), 7.08(1H, br), 7.50-7.54(2H, m), 7.63(1H, s), 7.70-7.72(2H, m), 7.94(1H, s), 8.08(1H, s) 1361 δ 0.87(3H, t, J=7.3Hz), 1.53-1.63(2H, m), 2.44-2.56(2H, m), 2.64(2H, t, J=7.8Hz), 4.38(2H, t, J=6.3Hz), 7.16(1H, s), 7.38(1H, t, J=7.8Hz), 7.48(1H, s), 7.61-7.64(2H, m), 7.91-7.94(2H, m), 8.00(1H, s) 1368 δ 0.93(3H, t, J=7.3Hz), 1.59-1.69(2H, m), 2.71(2H, t, J=7.8Hz), 4.86(2H, s), 7.11(1H, br), 7.49-7.54(2H, m), 7.62(1H, s), 7.69-7.72(2H, m), 7.96(1H, d, J=1.5Hz), 8.07(1H, s) 1385 δ 2.35(3H, s), 2.44(3H, s), 4.86(2H, s), 6.74(1H, s), 7.34-7.38(3H, m), 7.46(1H, s), 7.52(1H, d, J=8.8Hz), 7.89(1H, s), 8.35(1H, d, J=8.8Hz) 1386 δ 1.32(6H, d, J=6.3Hz), 2.40(6H, s), 2.41(3H, s), 5.03(1H, septet, J=6.3Hz), 6.46(1H, br-s), 7.15(1H, s), 7.28-7.37(4H, m), 7.95(1H, d, J=8.3Hz) 1387 δ 2.40(6H, s), 2.45(3H, s), 4.86(2H, s), 6.80(1H, br), 7.16(1H, s), 7.32-7.42(4H, m), 7.85(1H, br) 1388 δ1.35(3H, t, J=7.3Hz), 2.36(6H, s), 4.28(2H, q, J=7.3Hz), 6.91(1H, s), 7.29(1H, t, J=8.3Hz), 7.37(2H, s), 7.74-7.79(2H, m), 8.32(1H, br-d, J=5.9Hz) 1389 δ1.34(6H, d, J=6.3Hz), 2.36(6H, s), 5.07(1H, septet, J=6.3Hz), 6.86(1H, br-s), 7.30(1H, t, J=8.1Hz), 7.37(2H, s), 7.72-7.79(2H, m), 8.32(1H, br) 1408 δ 2.37(6H, s), 4.70(4H, dt, J=2.0Hz, 46.8Hz), 5.28(1H, tt, J=4.4Hz, 24.9Hz), 7.08(1H, br-s), 7.33(1H, t, J=8.3Hz), 7.37(2H, s), 7.76(1H, d, J=12.2Hz), 7.81(1H, dt, J=1.4Hz, 7.8Hz), 8.29(1H, br-s) 1411 δ 2.37(6H, s), 2.51-2.62(2H, m), 4.46(2H, t, J=6.4Hz), 6.97(1H, br- s), 7.32(1H, t, J=8.3Hz), 7.37(2H, s), 7.74-7.82(2H, m), 8.28(1H, br-s) 1416 δ 2.37(6H, s), 3.76-3.79(2H, m), 4.49(2H, t, J=5.4Hz), 7.02(1H, br), 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.74-7.81(2H, m), 8.30(1H, br) 1418 δ 2.37(6H, s), 4.88(2H, s), 7.21(1H, br), 7.32-7.37(3H, m), 7.76-7.85(2H, m), 8.31(1H, br) 1421 δ 2.36(6H, s), 3.60(2H, t, J=5.9Hz), 4.54(2H, t, J=5.9Hz), 7.03(1H, br), 7.32(1H, t, J=7.8Hz), 7.37(2H, s), 7.76-7.81(2H, m), 8.29(1H, br) 1435 δ1.35(3H, t, J=7.3Hz), 2.36(6H, s), 4.29(2H, q, J=7.3Hz), 6.89(1H, br-s), 7.30(1H, t, J=7.8Hz), 7.35(2H, s), 7.74-7.78(2H, m), 8.32(1H, br-s) 1455 δ 2.33(6H, s), 4.70(4H, ddd, J=48.8Hz, 2.4Hz, 4.3Hz), 5.28(1H, tt, J=20.0, 4.3Hz), 7.08(1H, br-s), 7.32(1H, d, J=8.3Hz), 7.35(2H, s), 7.75-7.83(2H, m), 8.29(1H, br-s) 1458 δ 2.36(6H, s), 2.51-2.62(2H, m), 4.47(2H, t, J=6.3Hz), 6.95(1H, br- s), 7.32(1H, t, J=7.3Hz), 7.35(2H, s), 7.74-7.82(2H, m), 8.29(1H, br-s) 1463 δ 2.36(6H, s), 3.77(2H, t, J=5.4Hz), 4.49(2H, t, J=5.4Hz), 7.03(1H, br), 7.31(1H, t, J=8.3Hz), 7.35(2H, s), 7.76-7.80(2H, m), 8.29(1H, br) 1465 δ 2.36(6H, s), 4.88(2H, s), 7.18(1H, br), 7.35(1H, t, J=8.3Hz), 7.36(2H, s), 7.75-7.85(2H, m), 8.31(1H, br) 1898 δ 1.33(6H, d, J=6.3Hz), 2.37(3H, s), 5.05(1H, septet, J=6.3Hz), 7.21(1H, br-s), 7.32(1H, d, J=6.6Hz), 7.39(1H, t, J=8.1Hz), 7.46(1H, s), 7.50-7.53(2H, m), 8.30-8.36(2H, m) 1899 δ 2.38(3H, s), 4.87(2H, s), 7.40-7.51(5H, m), 7.62(1H, s), 8.27-8.30(2H, m) 1900 δ 1.34(6H, d, J=6.1Hz), 2.41(6H, s), 5.05(1H, septet, J=6.1Hz), 7.22-7.26(2H, m), 7.31-7.40(4H, m), 8.33(1H, dd, J=1.5Hz, 8.1Hz) 1901 δ 2.40(6H, s), 4.88(2H, s), 7.29(1H, s), 7.37(2H, s), 7.38-7.43(2H, m), 7.50(1H, s), 8.28(1H, d, J=6.8Hz) 1902 δ 4.88(2H, s), 7.39(1H, dd, J=1.5Hz, 7.3Hz), 7.44-7.51(2H, m), 7.88-7.92(2H, m), 8.03(1H, s), 8.36(1H, d, J=8.3Hz), 8.70(1H, d, J=8.3Hz) 1903 δ 2.37(3H, s), 4.88(2H, s), 6.55(1H, septet, J=6.3Hz), 6.90(1H, s), 7.32(1H, s), 7.41-7.48(3H, m), 8.31(1H, br-s), 8.49(1H, s) 1904 δ 1.34(6H, d, J=6.3Hz), 2.44(6H, s), 5.05(1H, septet, J=6.3Hz), 7.13(1H, s), 7.25-7.28(2H, m), 7.37(2H, s), 7.41(1H, t, J=8.3Hz), 8.31(1H, dd, J=1.5Hz, 8.3Hz) 1905 δ 2.44(6H, s), 4.88(2H, s), 7.15(1H, br), 7.33-7.37(3H, m), 7.43-7.53(2H, m), 8.25(1H, d, J=8.3Hz) 1906 δ 2.40(3H, s), 4.86(2H, s), 7.05-7.10(2H, m), 7.47(1H, s), 7.53(1H, d, J=8.8Hz), 7.58(1H, br), 8.22(1H, br), 8.28(1H, d, J=8.8Hz). 1907 δ 2.40(6H, s), 4.86(2H, s), 7.00-7.11(3H, m), 7.37(2H, s), 8.18(1H, br) 1908 δ 1.33(6H, d, J=6.3Hz), 2.39(6H, s), 5.04(1H, septet, J=6.3Hz), 6.81(1H, br), 7.30(1H, br), 7.37(2H, s), 8.23(1H, br) 1909 δ 1.33(6H, d, J=6.1Hz), 2.34(3H, s), 2.42(3H, s), 5.05(1H, septet, J=6.1Hz), 6.46(1H, br), 7.30(1H, d, J=8.1Hz), 7.45(1H, s), 7.49(1H, d, J=8.5Hz), 7.60(1H, dd, J=1.7Hz, 8.1Hz), 7.83(1H, s), 8.27(1H, d, J=8.5Hz), 8.46(1H, br) 1910 δ 2.39(3H, s), 2.42(3H, s), 4.86(2H, s), 6.77(1H, br), 7.35(1H, d, J=8.1Hz), 7.46(1H, s), 7.50(1H, d, J=8.8Hz), 7.65(1H, dd, J=2.0Hz, 8.1Hz), 7.80(1H, s), 8.27(1H, d, J=8.8Hz), 8.36(1H, br) 1911 δ 1.33(6H, d, J=6.3Hz), 2.34(9H, s), 5.04(1H, septet, J=6.3Hz), 6.48(1H, br-s), 7.31(1H, d, J=7.8Hz), 7.34(2H, s), 7.55(1H, s), 7.64(1H, dd, J=1.5Hz, 7.8Hz), 8.46(1H, s) 1912 δ 2.34(6H, s), 2.40(3H, s), 4.86(2H, s), 6.78(1H, br), 7.34-7.36(3H, m), 7.50(1H, s), 7.69(1H, dd, J=1.5Hz, 7.8Hz), 8.36(1H, s) 1913 δ1.32(6H, d, J=6.3Hz), 2.43(3H, s), 3.96(3H, s), 5.05(1H, sept., J=6.3Hz), 6.98(1H, d, J=8.5Hz), 7.24(1H, s), 7.44(1H, s), 7.49(1H, d, J=8.5Hz), 7.71(1H, dd, J=2.2Hz, 8.5Hz), 7.82(1H, s), 8.25(1H, d, J=8.5Hz), 8.68(1H, s) 1914 δ 2.43(3H, s), 4.00(3H, s), 4.87(2H, s), 7.02(1H, d, J=8.5Hz), 7.45(1H, s), 7.50(1H, d, J=8.5Hz), 7.54(1H, s), 7.74-7.79(2H, m), 8.28(1H, d, J=8.5Hz), 8.66(1H, s) 1915 δ 1.33(6H, d, J=6.3Hz), 2.42(3H, s), 5.00-5.10(1H, m), 6.91(1H, br), 7.20(1H, dd, J=8.5Hz, 10.5Hz), 7.46(1H, s), 7.49(1H, d, J=8.8Hz), 7.62-7.66(1H, m), 7.82(1H, s), 8.20(1H, d, J=8.8Hz), 8.71(1H, d, J=6.1Hz) 1916 δ 2.46(3H, s), 4.87(2H, s), 7.23-7.29(2H, m), 7.47(1H, s), 7.51(1H, d, J=8.8Hz), 7.68-7.73(1H, m), 7.78(1H, s), 8.23(1H, d, J=8.5Hz), 8.68(1H, d, J=6.1Hz) 1917 δ 1.33(6H, d, J=6.3Hz), 2.34(6H, s), 5.04(1H, septet, J=6.3Hz), 6.91(1H, s), 7.20(1H, dd, J=8.5Hz, 10.5Hz), 7.35(2H, s), 7.56(1H, s), 7.66-7.70(1H, m), 8.71(1H, br-d, J=6.6Hz) 1918 δ 2.34(6H, s), 4.87(2H, s), 7.22(1H, dd, J=8.8Hz, 10.5Hz), 7.32(2H, s), 7.75-7.79(1H, m), 7.87(1H, s), 8.56(1H, s), 8.63(1H, br) 1919 δ1.34(6H, d, J=6.3Hz), 2.43(3H, s), 5.06(1H, septet, J=6.3Hz), 7.21(1H, s), 7.46(1H, s), 7.49-7.52(2H, m), 7.61(1H, dd, J=2.2Hz, 8.5Hz), 7.82(1H, s), 8.24(1H, d, J=8.5Hz), 8.78(1H, d, J=2.2Hz) 1920 δ 2.43(3H, s), 4.88(2H, s), 7.47(1H, s), 7.50-7.57(3H, m), 7.66(1H, dd, J=2.0Hz, 8.3Hz), 7.78(1H, s), 8.26(1H, d, J=8.3Hz), 8.72(1H, s) 1921 δ 1.34(6H, d, J=6.1Hz), 2.34(6H, s), 5.05(1H, septet, J=6.1Hz), 7.23(1H, s), 7.35(2H, s), 7.51(1H, d, J=8.3Hz), 7.63-7.69(2H, m), 8.76(1H, s) 1922 δ 2.35(6H, s), 4.88(2H, s), 7.36(2H, s), 7.50(1H, br), 7.53-7.59(2H, m), 7.70(1H, dd, J=2.0Hz, 8.3Hz), 8.72(1H, s) 1923 δ 2.35(6H, s), 2.45(3H, s), 4.84(2H, s), 7.00(1H, br), 7.36(2H, s), 7.41(1H, s), 7.48(2H, s), 7.83(1H, s) 1924 δ 1.33(6H, d, J=6.1Hz), 2.46(3H, s), 5.05(1H, septet, J=6.1Hz), 6.89(1H, br-s), 7.48(1H, s), 7.51(1H, d, J=9.1Hz), 7.79(2H, s), 7.89(1H, s), 8.18(1H, d, J=9.1Hz), 8.19(1H, s) 1925 δ 2.43(3H, s), 4.86(2H, s), 7.31(1H, br-s), 7.49(1H, s), 7.52(1H, d, J=8.8Hz), 7.78(1H, s), 7.85(1H, s), 7.94(1H, s), 8.18(1H, d, J=8.8Hz), 8.24(1H, s) 1926 δ 1.32(6H, d, J=6.1Hz), 2.34(6H, s), 5.04(1H, septet, J=6.1Hz), 6.87(1H, s), 7.36(2H, s), 7.50(1H, s), 7.83(1H, s), 7.90(1H, s), 8.20(1H, s) 1927 δ 2.35(6H, s), 4.86(2H, s), 7.26(1H, s), 7.37(2H, s), 7.48(1H, s), 7.89(1H, s), 7.97(1H, s), 8.24(1H, s) 1928 δ1.31(6H, d, J=6.3Hz), 2.33(6H, s), 3.89(2H, br.), 4.97-5.04(1H, m), 6.59(1H, s), 6.92(1H, s), 7.02(1H, s), 7.23-7.26(1H, m), 7.34(2H, s), 7.39(1H, br) 1929 δ 2.35(6H, s), 3.04(6H, s), 4.84(2H, s), 6.94(2H, br), 7.04(1H, s), 7.30(1H, s), 7.349(2H, s), 7.404(1H, s) 1930 δ 1.30(6H, d, J=6.3Hz), 2.37(3H, s), 2.48(3H, s), 5.02(1H, septet, J=6.3Hz), 6.57(1H, s), 7.20-7.28(2H, m), 7.44(2H, s), 7.50(1H, d, J=8.3Hz), 7.76(1H, s), 8.28(1H, d, J=9.1Hz) 1931 δ 2.39(3H, s), 2.48(3H, s), 4.84(2H, s), 7.22(1H, d, J=8.3Hz), 7.44-7.54(3H, m), 7.80(1H, s), 8.13(1H, d, J=8.1Hz), 8.20(1H, s), 9.04(1H, s) 1932 δ 1.30(6H, d, J=6.1Hz), 2.39(6H, s), 2.48(3H, s), 5.02(1H, septet, J=6.1Hz), 6.63(1H, s), 7.19-7.25(3H, m), 7.36(2H, s), 7.81(1H, s) 1933 δ 2.40(6H, s), 2.50(3H, s), 4.84(2H, s), 7.01(1H, br-s), 7.18(1H, s), 7.24-7.27(1H, m), 7.31-7.34(1H, m), 7.37(2H, s), 7.82(1H, s) 1934 δ 1.31(6H, d, J=6.1Hz), 2.41(3H, s), 5.04(1H, septet, J=6.1Hz), 6.69(1H, s), 7.16-7.21(1H, m), 7.46(1H, s), 7.5(1H, d, J=8.8Hz), 7.88(1H, dd, J=2.9Hz, 6.6Hz), 7.96(1H, br), 8.40(1H, d, J=8.8Hz), 8.57(1H, d, J=17.6Hz) 1935 δ 2.42(3H, s), 4.84(2H, s), 7.04(1H, br), 7.20-7.27(1H, m), 7.46(1H, s), 7.51(1H, d, J=8.5Hz), 7.94(1H, br), 8.01(1H, dd, J=2.9Hz, 6.6Hz), 8.40(1H, d, J=8.5Hz), 8.57(1H, br-d, J=17.6Hz) 1936 δ 1.31(6H, d, J=6.3Hz), 2.35(6H, s), 5.02(1H, septet, J=6.3Hz), 6.70(1H, s), 7.19(1H, dd, J=9.0Hz, 11.2Hz), 7.36(2H, s), 7.83(1H, dd, J=2.9Hz, 6.6Hz), 7.99(1H, br), 8.01(1H, d, J=5.1Hz) 1937 δ 2.36(6H, s), 4.84(2H, s), 7.10(1H, br-s), 7.21-7.26(1H, m), 7.36(2H, s), 7.94-8.03(3H, m) 1938 δ 1.31(6H, d, J=6.3Hz), 2.41(3H, s), 5.03(1H, septet, J=6.3Hz), 6.68(1H, s), 7.40(1H, d, J=8.8Hz), 7.46(1H, s), 7.51(1H, d, J=8.5Hz), 7.67(1H, d, J=8.5Hz), 7.78(1H, d, J=2.7Hz), 8.06(1H, s), 8.32(1H, d, J=8.8Hz) 1939 δ 2.42(3H, s), 4.84(2H, s), 7.38(1H, d, J=8.8Hz), 7.45-7.49(2H, m), 7.72(1H, d, J=7.3Hz), 7.93(1H, s), 8.17(1H, d, J=8.5Hz), 8.52(1H, s), 9.43(1H, s) 1940 δ 1.31(6H, d, J=6.1Hz), 2.40(6H, s), 5.03(1H, septet, J=6.1Hz), 6.70(1H, s), 7.36(2H, s), 7.41(1H, d, J=8.8Hz), 7.63-7.66(2H, m), 7.75(1H, d, J=2.7Hz) 1941 δ 2.40(6H, s), 4.84(2H, s), 7.08(1H, br), 7.37(2H, s), 7.46(1H, d, J=8.8Hz), 7.64-7.70(2H, m), 7.82(1H, d, J=2.7Hz) 1942 δ1.31(6H, d, J=6.3Hz), 2.41(3H, s), 4.97-5.07(1H, m), 6.70(1H, s), 7.45-7.58(4H, m), 7.72-7.75(2H, m), 8.30(1H, d, J=8.8Hz) 1943 δ 2.44(3H, s), 4.85(2H, s), 7.43-7.47(2H, m), 7.54(1H, d, J=8.5Hz), 7.61(1H, d, J=8.5Hz), 7.86(1H, s), 7.99(1H, d, J=8.1Hz), 9.09(1H, s), 9.89(1H, s) 1944 δ 2.43(3H, s), 4.84(2H, s), 7.36(1H, s), 7.44(1H, s), 7.47(1H, d, J=8.5Hz), 7.79(2H, d, J=8.5Hz), 8.08(1H, d, J=8.5Hz), 8.62(1H, s), 9.65(1H, s) 1945 δ 1.31(6H, d, J=6.3Hz), 2.45(6H, s), 5.03(1H, septet, J=6.3Hz), 6.66(1H, s), 7.16-7.21(2H, m), 7.36(2H, s), 7.76(1H, s), 7.82(1H, dd, J=2.7Hz, 8.8Hz) 1946 δ1.52(9H, s), 2.41(3H, s), 6.58(1H, s), 7.19(1H, dd, J=2.7Hz, 8.5Hz), 7.41(1H, s), 7.45(1H, s), 7.51(1H, d, J=7.1Hz), 7.69(1H, s), 7.79(1H, d, J=8.5Hz), 8.30(1H, d, J=8.5Hz) 1947 δ 2.44(3H, s), 2.45(3H, s), 4.83(2H, d, J=1.7Hz), 7.00(1H, br), 7.07-7.27(2H, m), 7.36(2H, s), 7.74-7.77(1H, d, J=10.3Hz), 7.86(1H, dd, J=8.5Hz, 10.3Hz) 1948 δ3.45(3H, s), 4.80(2H, s), 7.53-7.57(2H, m), 7.68(1H, s), 7.82(1H, d, J=7.8Hz), 7.93-7.95(3H, m) 1949 δ 2.30(3H, s), 3.41(3H, s), 4.77(2H, s), 6.77(1H, s), 6.95-7.00(1H, m), 7.07-7.16(2H, m), 7.29-7.41(4H, m) 1950 δ 1.26(6H, d, J=5.9Hz), 2.28(6H, s), 3.33(3H, s), 4.96(1H, septet, J=5.9Hz), 6.47(1H, s), 6.88(1H, d, J=7.8Hz), 7.04(1H, t, J=7.8Hz), 7.21(2H, s), 7.23-7.47(2H, m) 1951 δ 2.29(6H, s), 3.34(3H, s), 4.77(2H, s), 6.81(1H, br), 6.99(1H, d, J=7.8Hz), 7.10(1H, t, J=7.8Hz), 7.22(2H, s), 7.24-7.26(1H, m), 7.42(1H, s) 1954 δ 1.26(6H, d, J=6.3Hz), 2.34(3H, s), 3.34(3H, s), 4.97(1H, septet, J=6.3Hz), 6.46(1H, s), 6.99(1H, d, J=7.8Hz), 7.07(1H, t, J=7.8Hz), 7.28-7.31(2H, m), 7.40-7.44(1H, m), 7.62(1H, s) 1955 δ 2.35(3H, s), 3.36(3H, s), 4.77(2H, s), 7.02-7.13(3H, m), 7.29-7.37(2H, m), 7.44-7.52(1H, m), 7.62(1H, s) 1956 δ 1.26(3H, t, J=7.3Hz), 2.29(6H, s), 3.86(2H, q, J=7.3Hz), 4.76(2H, s), 6.86(1H, br), 6.92-6.95(1H, m), 7.08(1H, t, J=8.1Hz), 7.22(2H, s), 7.23-7.30(1H, m), 7.38(1H, t, J=2.0Hz) 1957 δ 1.46(6H, d, J=6.3Hz), 2.07(6H, s), 4.77(2H, s), 5.40(1H, septet, J=6.3Hz), 6.78(1H, br), 6.98(1H, d, J=7.8Hz), 7.14-7.19(1H, m), 7.17(2H, s), 7.29(1H, s), 7.46(1H, d, J=7.8Hz) 1958 δ 2.34(6H, s), 3.45(3H, s), 4.80(2H, s), 7.36(2H, s), 7.50-7.56(3H, m), 7.78(1H, d, J=6.1Hz), 7.90(1H, s) 1959 (DMSO-d₆) δ 2.32(6H, s), 3.30(3H, s), 4.86(2H, s), 6.83(1H, t, J=7.4Hz), 7.40(1H, t, J=7.4Hz), 7.44(2H, s), 7.67(1H, t, J=7.4Hz), 10.05(1H, s) 1960 δ1.29(6H, d, J=6.3Hz), 2.35(6H, s), 3.35(3H, s), 3.38(3H, s), 4.97-5.03(1H, m), 7.36(2H, s), 7.58(1H, s), 7.76(1H, s), 7.84(1H, s), 8.56(1H, s) 1961 (DMSO-d₆) δ 2.28(6H, s), 2.33(3H, s), 7.44(2H, s), 7.48(1H, t, J=7.8Hz), 7.66-7.75(2H, m), 8.11(1H, t, J=2.0Hz), 9.96(1H, s), 10.56(1H, s) 1962 (DMSO-d₆) δ1.34(3H, t, J=7.3Hz), 2.34(6H, s), 2.96(2H, q, J=7.3Hz), 7.33(2H, s), 7.41(1H, t, J=7.8Hz), 7.67(1H, d, J=7.8Hz), 7.83-7.85(1H, m), 8.11(1H, d, J=2.0Hz), 8.79(1H, s), 9.58(1H, s) 1963 δ 1.32(6H, d, J=6.6Hz), 2.37(6H, s), 5.00-5.06(1H, m), 6.69(1H, s), 7.35-7.65(5H, m), 8.09(1H, s), 8.72(1H, s) 1964 δ 2.37(6H, s), 4.85(2H, s), 7.07(1H, br.), 7.39(2H, s), 7.45(1H, t, J=8.1Hz), 7.61-7.68(2H, m), 8.11(1H, s), 8.69(1H, s) 1967 δ1.34(6H, d, J=6.3Hz), 2.34(6H, s), 5.09(1H, septet, J=6.3Hz), 7.29(1H, br-s), 7.35(2H, s), 7.91(1H, t, J=7.8Hz), 7.97(1H, d, J=7.8Hz), 8.21(1H, d, J=7.8Hz), 9.19(1H, br-s) 1968 δ 2.35(6H, s), 4.89(2H, s), 7.36(2H, s), 7.63(1H, br-s), 7.97(1H, dd, J=8.3Hz, 7.6Hz), 8.05(1H, d, J=7.6Hz), 8.21(1H, d, J=8.3Hz), 9.17(1H, br-s) 1969 δ 2.35(6H, s), 3.77-3.80(2H, m), 4.48-4.52(2H, m), 7.36(2H, s), 7.46(1H, br-s), 7.94(1H, t, J=7.8Hz), 8.02(1H, dd, J=7.8Hz, 1.0Hz), 8.19(1H, dd, J=7.8Hz, 1.0Hz), 9.17(1H, br-s) 2061 δ1.36(6H, d, J=6.4Hz), 2.52(6H, s), 5.07-5.14(1H, m), 7.36(2H, s), 7.56(1H, t, J=8.2Hz), 8.15(1H, dd, J=8.2Hz, 1.9Hz), 8.44(1H, dd, J=8.2Hz, 1.9Hz), 9.45(1H, br-s), 12.9(1H, br-s) 2062 δ 2.37(6H, s), 4.91(2H, s), 7.36(2H, s), 7.61(1H, t, J=8.3Hz), 8.23(1H, dd, J=8.3Hz, 1.9Hz), 8.45(1H, dd, J=8.3Hz, 1.9Hz), 9.81(1H, br-s), 12.7(1H, br-s) 2157 δ 2.36(6H, s), 4.90(2H, s), 7.38(2H, s), 7.52-7.60(2H, m), 8.44(1H, s), 8.56(1H, d, J=5.4Hz), 8.58(1H, br-s) 2164 δ1.33(6H, d, J=5.8Hz), 2.35(6H, s), 5.03-5.07(1H, m), 7.06(1H, s), 7.35(2H, s), 7.93(1H, d, J=2.4Hz), 7.95(1H, d, J=5.9Hz, 2.4Hz), 8.49(1H, d, J=5.9Hz), 9.58(1H, br-s) 2165 (DMSO-d₆)δ 2.26(6H, s), 5.02(2H, s), 7.43(2H, s), 7.75(1H, dd, J=5.4Hz, 2.0Hz), 8.31(1H, d, J=2.0Hz), 8.60(1H, d, J=5.4Hz), 10.41(1H, br-s), 10.92(1H, br-s) 2167 (DMSO-d₆)δ 2.36(6H, s), 4.90(2H, s), 7.34(2H, s), 7.94(1H, dd, J=7.3Hz, 3.4Hz), 8.31(1H, d, J=7.3Hz), 8.60(1H, d, J=3.4Hz), 10.90(1H, br-s), 13.65(1H, br-s) 2168 (DMSO-d₆)δ 2.30(6H, s), 3.61(3H, s), 5.03(2H, s), 7.47(2H, s), 7.92(1H, d, J=7.6Hz), 7.98(1H, d, J=7.6Hz), 8.08(1H, t, J=7.6Hz), 10.18(1H, s) I-1  δ 2.34(6H, s), 3.87(2H, br-s), 6.86-6.89(1H, m), 7.21-7.30(3H, m), 7.33(2H, s), 7.39(1H, s) I-2  δ 3.87(2H, br), 6.84-7.00(1H, m), 7.14-7.17(1H, m), 7.20(1H, t, J=2.0Hz), 7.24-7.28(1H, m), 7.60(2H, d, J=8.8Hz), 7.78(2H, d, J=8.8Hz), 7.90(1H, br-s) I-3  δ 2.51(3H, d, J=8.8Hz), 3.86(2H, br-s), 6.83-8.68(1H, m), 7.13-7.25(3H, m), 7.26-7.63(3H, m), 7.90(1H, br-s) I-4  δ3.87(2H, br-s), 3.89(3H, s), 6.86-6.88(1H, m), 6.99(1H, dd, J=8.6Hz, 2.0Hz), 7.15-7.20(2H, m), 7.27(1H, t, J=7.8Hz), 7.51(1H, d, J=8.6Hz), 7.83(1H, s), 7.93(1H, s) I-5  δ3.89(2H, br-s), 6.86-6.89(1H, m), 7.12-7.30(3H, m), 7.52-7.59(2H, m), 7.76-7.93(2H, m) I-6  δ 2.43(3H, s), 3.83(2H, br), 6.85-6.88(1H, m), 7.14-7.17(1H, m), 7.21-7.29(2H, m), 7.45(1H, s), 7.49(1H, d, J=8.8Hz), 7.76(1H, br), 8.27(1H, d, J=8.8Hz) I-7  δ 2.34(6H, s), 3.87(2H, br), 6.86-6.89(1H, m), 7.20-7.35(6H, m) I-8  δ 2.42(3H, s), 3.79(2H, br-s), 6.80(1H, dd, J=2.2Hz, 7.8Hz), 6.90(1H, d, J=7.8Hz), 7.05(1H, s), 7.15(1H, t, J=7.8Hz), 7.26-7.44(7H, m), 7.53(1H, s) I-9  δ 2.33(3H, s), 2.52(3H, d, J=8.8Hz), 3.89(2H, br-s), 6.86-6.89(1H, m), 7.14-7.16(1H, m), 7.22(1H, s), 7.28-7.30(2H, m), 7.65(1H, br-s), 8.11(1H, s) I-10 δ 2.28(3H, s), 2.46(3H, d, J=6.1Hz), 3.88(2H, br-s), 6.84-6.89(1H, m), 7.15-7.19(1H, m), 7.23-7.29(2H, m), 7.41(1H, d, J=9.1Hz), 7.73(1H, br-s), 7.81(1H, d, J=9.1Hz) I-12 δ 2.60(3H, s), 3.92(2H, br-s), 6.89-6.92(1H, m), 7.24-7.32(3H, m), 7.46(1H, s), 7.76(1H, br-s) I-13 δ 2.27(6H, s), 3.31(3H, s), 6.40-6.43(1H, m), 6.54-6.58(1H, m), 6.71(1H, t, J=2.0Hz), 6.76-6.86(1H, m), 7.22(2H, s) I-14 δ 1.45(6H, d, J=6.3Hz), 2.07(6H, s), 3.53(2H, br), 5.37(1H, septet, J=6.3Hz), 6.56-6.63(3H, m), 6.96(1H, t, J=7.8Hz), 7.16(2H, s) I-15 δ 1.32(3H, t, J=7.6Hz), 2.72(2H, q, J=7.6Hz), 3.88(2H, br), 6.85-6.89(1H, m), 7.13-7.14(1H, m), 7.22-7.30(2H, m), 7.46(1H, s), 7.50(1H, d, J=8.8Hz), 7.80(1H, br-s), 8.29(1H, d, J=8.8Hz) I-16 δ 1.17(3H, t, J=7.6Hz), 2.28(3H, s), 2.65(2H, q, J=7.6Hz), 3.85(2H, br-s), 6.82-6.85(1H, m), 7.21-7.23(3H, m), 7.34(2H, s), 7.64(1H, s) I-17 δ 1.22(6H, t, J=7.6Hz), 2.69(4H, q, J=7.6Hz), 3.86(2H, br-s), 6.86-6.89(1H, m), 7.15-7.36(4H, m), 7.38(2H, s) I-18 δ 1.23(3H, t, J=7.3Hz), 2.76(2H, q, J=7.3Hz), 3.88(2H, br-s), 6.88-6.91(1H, m), 7.26-7.32(3H, m), 7.50(1H, s), 7.53(1H, s), 7.95(1H, d, J=1.5Hz) I-19 δ 1.00(3H, t, J=7.3Hz), 1.65-1.75(2H, m), 2.67(2H, t, J=7.3Hz), 3.89(2H, br), 6.84-6.88(1H, m), 7.11-7.29(3H, m), 7.43(1H, s), 7.49(1H, d, J=8.5Hz), 7.85(1H, br-s), 8.27(1H, d, J=7.8Hz) I-20 δ1.22(6H, d, J=6.8Hz), 2.32(3H, s), 3.17(1H, septet, J=6.8Hz), 3.87(2H, br-s), 6.85-6.93(1H, m), 7.20-7.29(3H, m), 7.35(1H, s), 7.40-7.45(2H, m). I-21 δ 2.35(3H, s), 3.85(5H, s), 6.85-6.89(1H, m), 6.95(1H, s), 7.13(1H, s), 7.23-7.30(3H, m), 7.62(1H, s) I-22 δ 1.25(3H, t, J=7.6Hz), 2.76(2H, q, J=7.6Hz), 3.88(2H, br-s), 6.87-6.91(1H, m), 7.24-7.31(3H, m), 7.47(1H, s), 7.55(1H, s), 7.57(1H, s) I-23 δ 2.62(3H, d, J=6.4Hz), 3.91(2H, br-s), 6.89(1H, d, J=8.0Hz), 7.20-7.32(4H, m), 7.49(1H, d, J=9.0Hz), 8.58-8.60(1H, m) I-24 δ3.91(2H, br-s), 3.92(3H, s), 6.89-6.92(1H, m), 7.21-7.33(3H, m), 7.59(1H, d, J=1.2Hz), 8.50(1H, s), 8.54(1H, s) I-25 δ 2.35(3H, s), 2.57(3H, d, J=6.8Hz), 3.88(2H, br-s), 6.88-6.91(1H, m), 7.25-7.34(4H, m), 7.67(1H, s) I-26 δ 2.41(3H, s), 3.88(2H, br-s), 6.87-6.91(1H, m), 7.25-7.31(3H, m), 7.47(1H, s), 7.65(1H, s), 7.72(1H, s) I-27 δ 1.23(3H, t, J=7.3Hz), 2.74(2H, q, J=7.3Hz), 3.87(2H, br-s), 6.86-6.91(1H, m), 7.25-7.31(3H, m), 7.50(1H, s), 7.59(1H, s), 7.73(1H, d, J=1.5Hz) I-28 (DMSO-d₆)δ 0.84(3H, t, J=7.3Hz), 1.48-1.58(2H, m), 2.66(2H, t, J=7.3Hz), 5.36(2H, br-s), 6.77(1H, dd, J=1.0Hz, 7.8Hz), 7.10-7.19(3H, m), 7.59(1H, s), 7.80(1H, s), 10.03(1H, s) I-29 δ 0.90(3H, t, J=7.3Hz), 1.25-1.37(2H, m), 1.55-1.63(2H, m), 2.72(2H, t, J=7.8Hz), 3.89(2H, br), 6.87-6.91(1H, m), 7.24-7.31(3H, m), 7.48(1H, s), 7.55(1H, s), 7.73(1H, d, J=1.5Hz) I-30 δ 2.39(3H, s), 2.66(3H, d, J=6.9Hz), 7.43(1H, s), 7.75-7.79(2H, m), 8.33(1H, d, J=8.3Hz), 8.48(1H, d, J=8.3Hz), 8.80(1H, s) I-31 δ 2.41(3H, s), 3.88(2H, s), 6.86-6.91(1H, m), 7.28-7.32(3H, m), 7.49(1H, s), 7.58(1H, s), 7.93(1H, d, J=1.2Hz) I-32 δ 0.91(3H, t, J=7.3Hz), 1.58-1.67(2H, m), 2.69(2H, t, J=7.8Hz), 3.88(2H, br-s), 6.87-6.90(1H, m), 7.26-7.31(3H, m), 7.50(1H, s), 7.54(1H, s), 7.95(1H, d, J=2.0Hz) I-33 δ 2.33(6H, s), 3.87(2H, br-s), 6.86-6.89(1H, m), 7.21-7.29(3H, m), 7.34(2H, s), 7.52(1H, s) I-34 δ 2.32(6H, s), 3.86(2H, br-s), 6.85-6.88(1H, m), 7.20-7.28(3H, m), 7.33(2H, s), 7.60(1H, s) I-35 δ 3.86(2H, br), 6.84-6.87(1H, m), 7.13-7.28(3H, m), 7.63-7.64(2H, m), 7.70-7.74(2H, m), 7.91(1H, br-s) I-36 δ 3.99(2H, br-s), 6.85-6.88(1H, m), 7.23-7.34(3H, m), 7.91(2H, s), 8.69(1H, s) I-37 δ 3.91(2H, br), 6.88-6.91(1H, m), 7.15-7.21(2H, m), 7.29(1H, t, J=7.8Hz), 7.94-7.98(2H, m), 8.03(2H, d, J=8.8Hz), 8.11(1H, s) I-38 (DMSO-d₆)δ 5.39(2H, br-s), 6.77-6.80(1H, m), 7.12-7.19(3H, m), 8.49(2H, s), 10.53(1H, s) I-39 (DMSO-d₆)δ 2.30(3H, s), 4.32(2H, br-s), 4.39(2H, q, J=8.3Hz), 6.79-6.86(3H, m), 7.18-7.27(2H, m), 7.45(1H, d, J=8.8Hz), 7.56(1H, s), 8.91(1H, br-s) I-40 δ3.87(2H, br-s), 6.85-6.88(1H, m), 7.14(1H, dd, J=9.3Hz, 1.0Hz), 7.19(1H, t, J=2.0Hz), 7.27(1H, t, J=7.9Hz), 7.64(2H, d, J=8.7Hz), 7.71(2H, d, J=8.7Hz), 7.86(1H, s) I-42 δ3.88(2H, s), 6.90(1H, d, J=6.8Hz), 7.23-7.32(3H, m), 7.60(1H, s), 7.92(2H, s) I-43 δ3.89(2H, br-s), 6.90(1H, dt, J=2.5Hz, 6.3Hz), 7.25-7.32(3H, m), 7.59(1H, s), 7.72(2H, s) I-44 δ3.89(2H, br-s), 6.90(1H, dt, J=2.5Hz, 6.4Hz), 7.28-7.30(3H, m), 7.60(1H, s), 7.93(2H, s) I-45 δ3.92(2H, s), 6.92(1H, dt, J=1.5Hz, 7.3Hz), 7.23-7.30(3H, m), 7.79(1H, s), 8.04(2H, s) I-46 δ3.89(2H, br-s), 6.90(1H, dd, J=2.4Hz, 4.9Hz), 7.23-7.32(3H, m), 7.61(1H, s), 7.93(2H, s) I-47 δ3.88(2H, br-s), 6.90(1H, d, J=6.3Hz), 7.23-7.32(3H, m), 7.62(1H, s), 7.92(2H, s) I-48 δ6.90-6.94(1H, m), 7.28-7.33(3H, m), 7.73(1H, s), 8.02(1H, s), 8.25(1H, s) I-49 δ 2.31(6H, s), 2.90(3H, s), 6.81(1H, dd, J=1.9Hz, 7.8Hz), 7.15-7.18(2H, m), 7.30(1H, t, J=7.8Hz), 7.42(1H, s), 7.52(2H, s) I-50 δ 2.91(3H, s), 6.82-6.85(1H, m), 7.21-7.23(2H, m), 7.32(1H, t, J=7.8Hz), 7.64(1H, s), 7.93(2H, s) I-51 δ 2.29(3H, s), 2.34(3H, s), 3.82(2H, br), 6.81(1H, d, J=8.1Hz), 6.92(1H, d, J=8.1Hz), 7.11(1H, t, J=7.8Hz), 7.41-7.44(2H, m), 7.50(1H, d, J=8.3Hz), 8.36(1H, d, J=8.3Hz) I-53 δ 2.23(3H, s), 2.39(3H, s), 3.82(2H, br), 7.10-7.16(2H, m), 7.24(1H, d, J=1.7Hz), 7.44(1H, s), 7.49(1H, d, J=8.1Hz), 7.73(1H, s), 8.30(1H, d, J=8.8Hz) I-55 δ 2.34(3H, s), 2.40(3H, s), 3.70(2H, br), 6.72(1H, dd, J=2.4Hz, 8.1Hz), 6.83(1H, d, J=2.4Hz), 7.07(1H, d, J=8.1Hz), 7.36(1H, s), 7.44(1H, s), 7.50(1H, d, J=8.5Hz), 8.30(1H, d, J=8.5Hz) I-56 δ 2.38(6H, s), 2.42(3H, s), 3.70(2H, br), 6.72(1H, dd, J=2.4Hz, 8.1Hz), 6.89(1H, d, J=2.4Hz), 7.05(1H, s), 7.07(1H, d, J=8.1Hz), 7.36(2H, s) I-59 δ 2.37(6H, s), 3.90(2H, br-s), 6.96-7.01(1H, m), 7.10(1H, t, J=7.8Hz), 7.36(2H, s), 7.43-7.47(1H, m), 7.86(1H, d, J=13.2Hz) I-60 δ 2.33(6H, s), 6.99(1H, dt, J=1.5Hz, 7.8Hz), 7.10(1H, t, J=7.8Hz), 7.43(2H, s), 7.46(1H, d, J=7.8Hz), 7.84(1H, d, J=13.2Hz) I-61 δ 2.33(6H, s), 3.93(2H, s), 7.05-7.14(1H, m), 7.17-7.21(1H, m), 7.31(1H, s), 7.35(2H, s), 7.37-7.40(1H, m) I-62 δ 2.40(3H, s), 3.77(2H, br), 6.79-6.83(1H, m), 6.97-7.03(1H, m), 7.44-7.51(3H, m), 8.42(1H, d, J=8.8Hz), 8.60(1H, br-d, J=18.8Hz) I-63 δ 2.35(6H, s), 3.74(2H, br-s), 6.77-6.83(1H, m), 7.01(1H, dd, J=8.8Hz, 11.7Hz), 7.35(2H, s), 7.42(1H, dd, J=2.9Hz, 6.6Hz), 8.01(1H, d, J=15.6Hz) I-64 δ 2.38(3H, s), 4.27(2H, br), 6.89(1H, dd, J=1.5Hz, 8.1Hz), 7.05(1H, d, J=8.8Hz), 7.18(1H, t, J=8.1Hz), 7.45(1H, s), 7.51(1H, d, J=8.1Hz), 7.60(1H, s), 8.34(1H, d, J=8.8Hz) I-65 δ 2.40(6H, s), 4.27(2H, br-s), 6.88(1H, dd, J=1.5Hz, 7.8Hz), 7.03(1H, dd, J=1.5Hz, 7.8Hz), 7.16(1H, t, J=7.8Hz), 7.29(1H, s), 7.36(2H, s) I-66 δ 2.39(3H, s), 4.27(2H, br), 7.08(1H, dd, J=2.2Hz, 8.3Hz), 7.32-7.36(2H, m), 7.45(1H, s), 7.50(1H, d, J=8.5Hz), 7.68(1H, s), 8.24(1H, d, J=8.5Hz) I-67 δ 2.33(6H, s), 4.27(2H, br-s), 7.15(1H, d, J=8.1Hz), 7.35-7.38(5H, m) I-68 δ 2.41(3H, s), 3.87(2H, br), 6.73(1H, dd, J=2.9Hz, 8.5Hz), 7.18(1H, d, J=2.9Hz), 7.21(1H, d, J=8.8Hz), 7.45(1H, s), 7.50(1H, d, J=8.8Hz), 8.12(1H, s), 8.34(1H, d, J=8.5Hz) I-69 δ 2.39(6H, s), 3.85(2H, br-s), 6.72(1H, dd, J=2.7Hz, 8.5Hz), 7.15(1H, d, J=2.7Hz), 7.22(1H, d, J=8.5Hz), 7.36(2H, s), 7.66(1H, s) I-70 δ 2.43(6H, s), 4.34(2H, br), 6.86(1H, dd, J=1.5Hz, 8.3Hz), 6.96(1H, dd, J=1.5Hz, 8.3Hz), 7.13(1H, s), 7.19(1H, t, J=8.3Hz), 7.36(2H, s) I-71 δ 2.41(3H, s), 3.87(2H, br), 6.66(1H, dd, J=2.9Hz, 8.5Hz), 7.03(1H, d, J=2.9Hz), 7.38(1H, d, J=8.5Hz), 7.45(1H, s), 7.50(1H, d, J=8.5Hz), 7.75(1H, br-s), 8.33(1H, d, J=8.5Hz) I-72 δ 2.40(3H, s), 3.94(2H, br), 7.05-7.16(2H, m), 7.36(1H, dd, J=2.2Hz, 8.5Hz), 7.45(1H, s), 7.50(1H, d, J=9.0Hz), 7.66(1H, s), 8.24(1H, d, J=9.0Hz) I-73 δ 2.41(3H, s), 3.88(2H, br-s), 6.54(1H, dd, J=2.9Hz, 8.5Hz), 6.88(1H, d, J=2.9Hz), 7.37(1H, s), 7.45(1H, s), 7.52(1H, d, J=8.3Hz), 7.61(1H, d, J=8.3Hz), 8.32(1H, d, J=8.5Hz) I-74 δ 2.44(6H, s), 3.86(2H, br-s), 6.52(1H, dd, J=2.9Hz, 8.5Hz), 6.91(1H, d, J=2.9Hz), 7.12(1H, s), 7.35(2H, s), 7.62(1H, d, J=8.5Hz) I-75 δ 2.38(3H, s), 4.39(2H, s), 7.06(1H, s), 7.40(1H, d, J=1.7Hz), 7.43-7.50(3H, m), 7.90(1H, d, J=9.1Hz), 8.73(1H, s) I-76 δ 2.27(6H, s), 4.09(2H, br-s), 7.08(1H, s), 7.33(2H, s), 7.37(1H, s), 7.43(1H, s), 7.83(1H, s) I-77 δ 2.39(3H, s), 2.93(3H, s), 3.95(2H, br), 6.84(1H, d, J=8.3Hz), 7.21-7.27(2H, m), 7.44(1H, s), 7.48(1H, d, J=8.5Hz), 7.69(1H, s), 8.28(1H, d, J=8.5Hz) I-79 δ 2.33(6H, s), 3.76(4H, br), 6.19(1H, d, J=2.0Hz), 6.60(2H, d, J=2.0Hz), 7.34(1H, br), 7.52(2H, s) I-80 δ 2.38(3H, s), 4.65(2H, s), 7.26(1H, s), 7.34(1H, s), 7.47(1H, s), 7.52(1H, d, J=8.5Hz), 8.20(1H, d, J=8.5Hz) I-81 δ 2.50(3H, s), 3.90(2H, s), 6.91-6.94(1H, m), 7.27-7.35(3H, m), 7.48-7.57(2H, m), 7.70(1H, s), 7.75(1H, s), 8.01-8.04(1H, m), 8.45-8.48(1H, m) I-82 δ1.74-1.78(2H, m), 1.82-1.88(2H, m), 2.72(2H, t, J=6.0Hz), 3.01(2H, q, J=6.0Hz), 3.88(2H, br-s), 6.85-6.88(1H, m), 7.14-7.16(1H, m), 7.22-7.29(2H, m), 7.42(1H, d, J=8.6Hz), 7.70(1H, br-s), 8.10(1H, d, J=9.0Hz) I-83 δ1.71-1.79(4H, m), 2.81(2H, t, J=6.1Hz), 2.99(2H, q, J=6.3Hz), 3.87(2H, br-s), 6.87-6.90(1H, m), 7.24-7.29(3H, m), 7.47-7.52(2H, m) I-84 δ3.87(2H, br-s), 6.51(1H, septet, J=6.3Hz), 6.85-6.88(1H, m), 6.99(1H, d, J=8.7Hz), 7.15(1H, d, J=7.3Hz), 7.20(1H, t, J=2.0Hz), 7.25-7.29(1H, m), 7.75(1H, br-s), 8.15(1H, dd, J=8.7Hz, 2.4Hz), 8.30(1H, d, J=2.4Hz) I-85 δ 2.37(3H, s), 4.27(2H, br-s), 6.55(1H, septet, J=6.3Hz), 6.88-6.91(2H, m), 7.06(1H, dd, J=7.3Hz, 1.5Hz), 7.18(1H, t, J=7.3Hz), 7.37(1H, br-s), 8.50(1H, br-s) I-86 δ 2.37(3H, s), 3.88(2H, br-s), 6.34(1H, septet, J=6.3Hz), 6.88(1H, s), 6.89-6.91(1H, m), 7.23-7.31(3H, m), 7.47(1H, br-s)

The insecticides containing the compounds represented by formula (1) of the present invention as active ingredients are suitable for preventing insect pests such agricultural, horticultural and stored grain insect pests which are noxious to paddy rice, fruit trees, vegetables, other crops and flowing plants, sanitary pests, or nematodes. For example, the insecticides have strong insecticidal activity on the following insect pests: Lepidoptera such as cotton caterpillar (Diaphania indica), oriental tea tortrix (Homona magnanima), cabbage webworm (Hellulla undalis), summer fruit tortrix(Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), apple tortrix (Archips fuscocupreanus), peach fruit moth (Carposina niponensis), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), citrus leafminer (Phyllocnistis citrella), persimmon fruit moth (Stathmopoda masinissa), tea leafroller (Caloptilia theivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), small citrus dog (Papilio xuthus), common cabbage worm (Pieris rapae crucivora), tabacco budworm (Heliothis armigera), codling moth (Lapsey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tabacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), paddy borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), black cutworm (Agrotis ipsilon), turnip moth (Agrotis segetum), beet semi-looper (Autographa nigrisigna), and cabbage looper (Trichoplusia ni); hemiptera such as aster leafHopper (Macrosteles fascifrons), green rice leafHopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), silverleaf whitefly (Bermisia argentifolii), sweetpotato whitefly (Bemisia tabaci), greenHouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii), apple aphid (Aphis Citricola), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), Comstock mealybug (Pseudococcus Comstocki), Japanese mealybug (Planococcus kraunhiae), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), San Jose scale (Comstockaspis perniciosa), arrowHead scale (Unaspis yanonensis), brownwinged green bug (Plautia Stali), and brown marmorated stink bug (Halyomorpha mista); Coleoptera such as soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), cigarette beetle (Lasioderma serricorne), powderpost beetle (Lyctusbrunneus), twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), adzuki been weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), yellowspotted longicorn beetle (Psacothea hilaris), and whitespotted longicorn beetle (Anoplophora malasiaca); Diptera such as melon fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), house fly (Musca domestica), garden pea leafminer (Chromatomyia horticola), legume leafminer (Liriomyza trifolii), bryony leafminer (Liriomyza bryoniae), and common house mosquito (Culex pipiens pipiens); Nematoda such as coffee root-lesion nematode (Pratylenchus coffeae), root-lesion nematode (Pratylenchus sp.), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylemchulus semipenetrans), nematode (Aphelenchus avenae), and chrysanthemum foliar nematode (Aphelenchoides ritzemabosi); Thysanoptera such as melon thrips (Thrips palmi), western flower thrips (Frankliniella occidentalis), yellow tea thrips (Scirtothrips dorsalis), honeysuckle thrips (Thrips flavus), and onion thrips (Thrips tabaci); Orthoptera such as German cockroach (Blattella germanica), American cockroach (Periplaneta americana), and rice grasshopper (Oxya yezoensis).

The insecticides containing the compounds represented by formula (1) of the present invention as active ingredients have a significant preventive effect on the above-described insect pests noxious to lowland crops, dry field crops, fruit trees, vegetables, other crops, and flowering plants. The effect as the insecticides of the present invention can be achieved by treating paddy water, foliages or soil of paddy fields, dry fields, fruit trees, vegetables, other crops, or flowering plants before the breeding of noxious insects or at the time of observation of the breeding of noxious insects at the predicted breeding season of noxious insects.

The insecticides of the present invention are generally formed into formulations suitable for use according to a normal method for formulating agricultural/Horticultural pesticides. Namely, a compound represented by formula (1) may be mixed with an appropriate inert carrier, and if required, an auxiliary at a proper proportion, and the resultant mixture is subjected to dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion to form a suitable formulation such as a suspension, an emulsion, a liquid drug, a wettable powder, a granule, a dusting powder, or a tablet. As the inert carrier used in the present invention, either a solid or a liquid may be used. Examples of a material usable as the solid carrier include soybean flour, grain flour, wood flour, bark flour, sawing flour, tobacco stalk flour, walnut sHell flour, bran, cellulose powder, a residue after plant extraction, a synthetic polymer such as a synthetic resin powder, clay (for example, kaoline, bentonite, or acid white clay), talc (for example, talc or pyrophyllite), silica (for example, diatomite, silica powder, mica, white carbon (synthetic high-dispersion silicate referred to as “hydrous silicate fine powder” or “hydrous silicate”, some products containing calcium silicate as main components)), activated carbon, sulfur powder, pumice, calcined diatomite, brick powder, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonoium nitrate, urea, and ammonium chloride, and compost. These carriers are used alone or in a mixture of at least two kinds.

As a material usable as the liquid carrier, a material having a solvent ability or a material having no solvent ability but having an ability to disperse an active ingredient compound with the aid of an auxiliary is selected. Typical examples of the liquid carrier are given below, and these examples can be used alone or in a mixture of two more kinds. Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, and ethylene glycol); ketones (for example, acetone, methylethyl ketone, methyl isobutyl ketone, diisobutyl ketone, and cyclohexanone); ethers (for example, diethyl ether, dioxane, cellosolve, diisopropyl ether, and tetrahydrofuran); aliphatic hydrocarbons (for example, kerosine and mineral oil); aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, and alkylnaphthalene); halogenated hydrocarbons (for example, dichloromethane, chloroform, carbon tetrachloride, and chlorobenzene); esters (for example, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, and dioctyl phthalate); amides (for example, dimethylformamide, diethylformamide, and dimethylacetamide); and nitriles (for example, acetonitrile).

Typical examples of other auxiliaries are given below, and these examples are used alone or in combination according to purposes. The auxiliary is not necessarily used. For example, a surfactant is used for emulsifying, dispersing, solubilizing and/or wetting the active ingredient compound. Examples of the surfactant include

polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalenesulfonate, lignin-sulfonate, higher alcohol sulfates. Examples of other auxiliaries used for stabilizing dispersion of the active ingredient compound, and tackifying and/or bonding the active ingredient compound are given below. Examples of such auxiliaries include casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohol, wood turpentine, bran oil, bentonite, xanthan gum, and lignin-sulfonate.

Another auxiliary for improving fluidity of a solid product can also be used. Examples of such an auxiliary include wax, stearates, and alkyl phosphates. Also, an auxiliary such as a naphthalenesulfonic acid condensate or condensed phosphate, can be used as a deflocculant for a suspending product. Furthermore, an auxiliary such as silicone oil can be used as a defoaming agent.

The compounds represented by formula (1) of the present invention are stable to light, heat and oxidation. However, an appropriate amount of an antioxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methyl phenol) or BHA (butylated hydroxyanisole), a bisphenol derivative, an arylamine such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, or a condensate of phenetidine and acetone, or a benzophenone compound, may be added as a stabilizer to produce compositions having a stable effect.

When a compound represented by formula (1) of the present invention is used as an active ingredient, generally, the amount thereof used in a dust is 0.5% by weight to 20% by weight, the amount in an emulsion is 5% by weight to 50% by weight, the amount in a wettable powder is 10% by weight to 90% by weight, the amount in a granule is 0.1% by weight to 20% by weight, and the amount in a flowable formulation is 10% by weight to 90% by weight. With respect to the amount of the carrier in a formulation, the amount in a dust is 60% by weight to 99% by weight, the amount in an emulsion is 40% by weight to 95% by weight, the amount in a wettable powder is 10% by weight to 90% by weight, the amount in a granule is 80% by weight to 99% by weight, and the amount in a flowable formulation is 10% by weight to 90% by weight. With respect to the amount of the auxiliary in a formulation, the amount in a dust is 0.1% by weight to 20% by weight, the amount in an emulsion is 1% by weight to 20% by weight, the amount in a wettable powder is 0.1% by weight to 20% by weight, the amount in a granule is 0.1% by weight to 20% by weight, and the amount in a flowable formulation is 0.1% by weight to 20% by weight.

In order to prevent various noxious insects, the compound of the present invention is directly used or properly diluted with water or suspended in water, and an effective amount thereof for preventing pests is applied to crops in which the breeding of the noxious insects is predicted, or a place where the breeding of the noxious insects is undesirable. The amount of the compound used depends upon the various factors, for example, the purpose, the object insects, the growth conditions of crops, the breeding tendency of insects, weather, environmental conditions, formulations, application methods, application places, and application times. However, the content of the active ingredient used is generally 0.0001 ppm to 5000 ppm, and preferably 0.01 ppm to 1000 ppm. The amount of the active ingredient per 10 a is generally 1 g to 300 g.

An insecticide containing as an active ingredient the compounds represented by formula (1) of the present invention may be singly used for preventing insect pests such agricultural, horticultural or stored grain insect pests which are noxious to paddy rice, fruit trees, vegetables, other crops and flowering plants, sanitary pests, or nematodes. In order to further obtain an excellent preventive effect on various noxious insects which simultaneously occur, at least one of other insecticides and/or fungicides may be combined with the compounds represented by formula (1) of the present invention.

Examples of such insecticides which can be combined with the compounds represented by formula (1) of the present invention include synthetic pyrethroid insecticides such as allethrin, tetramethrin, resmethrin, phenothrin, furamethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropathrin, tralomethrin, cycloprothrin, flucythrinate, fluvalinate, acrinathrin, tefluthrin, bifenthrin, empenthrin, beta-cyfluthrin, zeta-cypermethrin, and fenvalerate, and various isomers thereof and pyrethrum extracts; organophosphate insecticides such as DDVP, cyanophos, fenthion, fenitrothion, tetrachlorvinphos, dimethylvinphos, propaphos, methylparathion, temephos, phoxim, acephate, isofenphos, salithion, DEP, EPN, ethion, mecarbam, pyridafenthion, diazinon, pirimiphos-methyl, etrimfos, isoxathion, quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet, methidathion, oxydeprofos, vamidothion, malathion, phenthoate, dimethoate, formothion, thiometon, ethylthiometon, phorate, terbufos, profenofos, prothiofos, sulprofos, pyraclofos, monocrotophos, naled, fosthiazate, and cadusafos; carbamate insecticides such as NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, ethiofencarb, bendiocarb, pirimicarb, carbosulfan, benfuracarb, methomyl, oxamyl, and aldicarb; arylpropylether insecticides such as etofenprox and halfenprox; silylether insecticides such as silafluofen; insecticidal natural products such as nicotine-sulfate, polynactin complex, abamectin, milbemectin, and BT agents; insecticides such as, cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil, buprofezin, fenoxycarb, pyriproxyfen, methoprene, hydroprene, kinoprene, diafenthiuron, triazamate, tebufenozide, and endosulfan; acaricides such as dicofol, chlorobenzilate, bromopropylate, tetradifon, CPCBS, BPPS, chinomethionate, amitraz, benzoximate, hexythiazox, fenbutatin oxide, cyhexatin, dienochlor, clofentezine, pyridaben, fenpyroximate, fenazaquin, and tebufenpyrad; and other insecticides such as novaluron, noviflumuron, emamectin benzoate, clothianidin, thiacloprid, thiamethoxam, flupyrazofos, acequinocyl, bifenazate, chromafenozide, etoxazole, fluacrypyrim, flufenzine, halofenozide, indoxacarb, methoxyfenozide, spirodiclofen, tolfenpyrad, gamma-cyhalothrin, ethiprole, amidoflumet, bistrifluron, flonicamid, flubrocythrinate, flufenerim, pyridalyl, pyrimidifen, spinosad, and spiromesifen.

Examples of fungicides which can be combined with the compounds represented by formula (1) of the present invention include azole fungicides such as triadimefon, hexaconazole, propiconazole, ipconazole, prochloraz, and triflumizole; pyrimidine fungicides such as pyrifenox and fenarimol; anilinopyrimidine fungicides such as mepanipyrim and cyprodinil; acylalanine fungicides such as metalaxyl, oxadixyl, and benalaxyl; benzimidazole fungicides such as thiophanate-methyl and benomyl; dithiocarbamate fungicids such as mancozeb, propineb, zineb, and metiram; organochlorine fungicides such as tetrachloroisophthalonitrile; carboxamide fungicides such as carpropamid and ethaboxam; morpholine fungicides such as dimethomorph; strobilurin fungicides such as azoxystrobin, kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin; dicarboxyimide fungicides such as iprodione and procymidone; soil-applied fungicides such as flusulfamide, dazomet, methyl isothiocyanate, and chloropicrin; copper fungicides such as basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, oxine-copper, and DBEDC; inorganic fungicides such as sulfur and zinc sulfate; organophosphate fungicides such as edifenphos, tolclofos-methyl, and fosetyl-aluminum; melanin biosynthesis inhibitors such as phthalide, tricyclazole, pyroquilon, and diclocymet; antibiotics such as kasugamycin, validamycin, and polyoxins; fungicidal natural products such as repe seed oil; and other fungicides such as benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid, quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid, proquinazid, silthiofam, oxypoconazole, famoxadone, cyazofamid, fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole, chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet, dichlofluanid,

(RS)—N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide(penthiopyrad; ISO proposed), oxycarboxin, mepronil, flutolanil, triforine, oxolinic acid, probenazole, acibenzolar-5-methyl, isoprothiolane, ferimzone, diclomezine, pencycuron, fluoroimide, chinomethionate, iminoctadine-triacetate, and iminoctadine-albesilate.

When the compounds represented by formula (1) of the present invention are combined with at lease one type of other insecticide and/or fungicide, mixed compositions of the compounds represented by formula (1) and other insecticides and/or fungicides may be used, or the compounds represented by formula (1) may be mixed with other insecticides and/or fungicides during agricultural treatment.

Besides the above-described insecticides and fungicides, the compounds represented by formula (1) may be mixed with a herbicide, a fertilizer, an ameliorant, a plant protective such as a plant growth regulator, or resources to form multipurpose compositions having superior efficiency or compositions from which an additive effect or a synergistic effect can be expected.

Although representative examples of the present invention will be described below, the present invention is not limited to these examples.

EXAMPLE 1

(1-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

To a solution prepared by adding 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine to 100 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 13.0 g of 3-nitrobenzoyl chloride in 20 ml of tetrahydrofuran. After the resultant mixture was stirred at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with a n-hexane-diisopropyl ether solvent mixture to obtain 26.0 g (yield 85%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J=8.1 Hz), 8.28 (1H, d, J=8.1 Hz), 8.44 (1H, dd, J=1.2 Hz, 8.1 Hz), 8.75 (1H, t, J=1.2 Hz)

(1-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide

To a solution prepared by adding 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 1.56 g of tin chloride anhydride to 25 ml of ethanol and stirring the resultant mixture at room temperature was added 2 ml of conc. hydrochloric acid. The resultant mixture was then stirred under heating at 60° C. for 1 hour. After the temperature was returned to room temperature, the reaction solution was poured into water and then neutralized with potassium carbonate. Then, ethyl acetate was added to the reaction solution, and insoluble materials were filtered off. Then, an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.44 g (yield 53%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)

(1-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-chloroethoxycarbonylamino)benzamide (Compound No. 130)

To a solution prepared by adding 0.20 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.08 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.07 g of 2-chloroethyl chloroformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.23 g (yield 91%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 2.35 (6H, s), 3.74-3.77 (2H, m), 4.44-4.47 (2H, m), 6.87 (1H, broad), 7.36 (2H, s), 7.43-7.52 (2H, m), 7.59-7.64 (2H, m), 8.02 (1H, s)

The compounds shown in Table 6 can be produced as production intermediates useful for producing the compounds represented by formula (1) of the present invention according to the processes described in Examples 1-1 and 1-2.

EXAMPLE 2

Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(ethylthiocarbonylamino)benzamide (Compound No. 1962)

To a solution prepared by adding 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide produced in (1-2) of Example 1 and 0.06 g of pyridine to 5 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 0.08 g of ethyl chlorothioformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution. Then, a separating operation was performed, and an organic layer was separated and then dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.27 g (yield 89%) of the title compound as a white solid.

¹H-NMR (CDCl₃+DMSO-d₆, ppm) δ 1.34 (3H, t, J=7.3 Hz), 2.34 (6H, s), 2.96 (2H, q, J=7.3 Hz), 7.33 (2H, s), 7.41 (1H, t, J=7.8 Hz), 7.67 (1H, d, J=7.8 Hz), 7.83-7.85 (1H, m), 8.11 (1H, d, J=2.0 Hz), 8.79 (1H, s), 9.58 (1H, s)

EXAMPLE 3

Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(4-cyanobenzyl)oxycarbonylamino]benzamide (Compound No. 85)

To a solution prepared by adding 0.30 g 3-isocyanatobenzoyl chloride to 10 ml of ether and then stirring the resultant mixture at 2° C. was dropwise added, over 5 minutes at a temperature kept at 2° C., a solution of 0.23 g of 4-cyanobenzyl alcohol and 0.32 g of tri-n-butylamine in 5 ml of ether. After the resultant mixture was stirred at 2° C. for 2 hours, the temperature was returned to room temperature, and then a solution of 0.49 g of 2,6-dimethyl-4-heptafluoroisopropylaniline in 5 ml of ether was dropwise added to the mixture, followed by stirring at room temperature for 3 hours. Then, ethyl acetate was added to the reaction solution, and the reaction solution was washed with water twice. Then, an organic layer was dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1 to 1:1) to obtain 0.50 g (yield 40%) of the title compound as an oily material.

¹H-NMR (CDCl, ppm) δ 2.34 (6H, s), 5.27 (2H, s), 6.97 (1H, broad-s), 7.35 (2H, s), 7.45-7.52 (4H, m), 7.61-7.69 (4H, m), 8.01 (1H, s)

Similarly, N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzamide (Compound No. 163) was produced by using 2-chloro-5-hydroxymethylpyridine.

¹H-NMR (CDCl₃, ppm) δ 2.34 (6H, s), 5.22 (2H, s), 6.89 (1H, broad-s), 7.35-7.49 (5H, m), 7.62 (2H, d, J=7.3 Hz), 7.72-7.77 (1H, m), 8.00 (1H, broad-s), 8.45 (1H, d, J=2.4 Hz)

N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(tetrahydrofuran-3-yl)methoxycarbonylamino]benzamide (Compound No. 158) was produced by the same process as described above using 3-hydroxymethyltetrahydrofuran except that the solvent was changed to tetrahydrofuran.

¹H-NMR (CDCl₃, ppm) δ 1.66-1.73 (1H, m), 2.05-2.13 (1H, m), 2.34 (6H, s), 2.60-2.70 (1H, m), 3.64-3.68 (1H, m), 3.73-3.79 (1H, m), 3.85-3.92 (2H, m), 4.09-4.15 (2H, m), 6.87 (1H, broad-s), 7.35 (2H, s), 7.46 (2H, t, J=7.8 Hz), 7.61-7.66 (2H, m), 8.01 (1H, broad-s)

EXAMPLE 4

(4-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide

To 10 ml of toluene were added 0.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide produced in Example (1-2) and 0.19 g of Lawesson's reagent. Then, the resultant mixture was stirred under heating at a reflux temperature for 6 hours. The reaction solution was concentrated under reduced pressure, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=3:1) to obtain 0.07 g (yield 20%) of the title compound.

¹H-NMR (CDCl₃, ppm) δ 2.36 (6H, s), 3.87 (2H, broad-s), 6.84-6.87 (1H, m), 7.18-7.24 (2H, m), 7.33 (1H, s), 7.39 (2H, s), 8.56 (1H, broad-s)

(4-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzthioamide (Compound No. 1964)

To a solution prepared by adding 0.07 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide and 0.03 g of pyridine to 5 ml of tetrahydrofuran and then stirring the resultant mixture at room temperature was dropwise added a solution of 0.05 g of 2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.09 g (yield 90%) of the title compound as a white solid.

¹H-NMR(CDCl₃, ppm) δ 2.37 (6H, s), 4.85 (2H, s), 7.07 (1H, broad), 7.39 (2H, s), 7.45 (1H, t, J=8.1 Hz), 7.61-7.68 (2H, m), 8.11 (1H, s), 8.69(1H, s)

EXAMPLE 5

(5-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridine-2-carboxamide

First, to a solution prepared by adding 2.36 g of 6-chloropyridine-2-carboxylic acid and 5 droplets of N,N-dimethylformamide to 30 ml of toluene was added 2.14 g of thionyl chloride, and then the resultant mixture was stirred under heating at 80° C. for 2 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. The resultant solution was added dropwise, at room temperature, to a solution obtained by adding 3.83 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.28 g of pyridine to 20 ml of tetrahydrofuran, followed by stirring for 5 hours. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 3.90 g (yield 67%) of the title compound as a solid.

¹H-NMR(CDCl₃, ppm) δ 2.36 (6H, s), 7.36 (2H, s), 7.56 (1H, dd, J=1.0 Hz, 8.1 Hz), 7.88 (1H, dd, J=7.6 Hz, 8.1 Hz), 8.23 (1H, dd, J=1.0 Hz, 7.6 Hz), 9.27 (1H, broad-s)

(5-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-aminopyridine-2-carboxamide

In a 200 ml autoclave were charged 3.08 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridien-2-carboxamide, 30 ml of 28% ammonia water, 0.20 g of copper sulfate, and 70 ml of methanol, and the resultant mixture was stirred under heating at 150° C. for 2 hours. After the mixture was cooled to room temperature, ammonia was distilled off at 60° C. under atmospheric pressure, and methanol was distilled off under reduced pressure. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous sodium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:2 to 2:3) to obtain 2.90 g (yield 98%) of the title compound as a oily material.

¹H-NMR (CDCl₃, ppm) δ 2.35 (6H, s), 4.57 (2H, broad-s), 6.69-6.74 (1H, m), 7.34 (2H, s), 7.62-7.66 (2H, m), 9.39 (1H, broad-s)

(5-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(2,2,2-trichloroethoxycarbonylamino)pyridine-2-carboxamide (Compound No. 1968)

To a solution prepared by adding 0.15 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-aminopyridine-2-carboxamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.085 g of 2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 0.13 g (yield 61%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 2.35 (6H, s), 4.89 (2H, s), 7.36 (2H, s), 7.63 (1H, broad-s), 7.97 (1H, dd, J=7.6 Hz, 8.3 Hz), 8.05 (1H, d, J=7.6 Hz), 8.21 (1H, d, J=8.3 Hz), 9.17 (1H, broad-s)

(5-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(2,2,2-trichloroethoxycarbonylamino)pyridine-N-oxide-2-carboxamide (Compound No. 2062)

To 10 ml of benzene was added 0.26 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(2,2,2-trichloroethoxycarbonylamino)pyridine-2-carboxamide produced in Example 5-3, and then the resultant mixture was stirred. Then, 0.08 g of m-chloroperbenzoic acid was added to the mixture at room temperature. After the resultant mixture was stirred at 70° C. for 1 hour, 0.2 g of m-chloroperbenzoic acid was further added to the mixture, followed by stirring at 70° C. for 7 hours. Then, the mixture was diluted with ethyl acetate, and an organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate three times and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 0.11 g (yield 41%) of the title compound as an amorphous material.

¹H-NMR (CDCl₃, ppm) δ 2.37 (6H, s), 4.91 (2H, s), 7.36 (2H, s), 7.61 (1H, t, J=8.3 Hz), 8.23 (1H, dd, J=8.3 Hz, 1.9 Hz), 8.45 (1H, dd, J=8.3 Hz, 1.9 Hz), 9.81 (1H, broad-s), 12.70 (1H, broad-s)

(5-5) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(methylamino)pyridine-2-carboxamide

N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(methylamino)pyridine-2-carboxamide was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridine-2-carboxamide produced in Example 5-1 and a methylamine aqueous solution as reaction materials according to the process described in Example 5-2.

¹H-NMR (DMSO-d₆, ppm) δ 2.30 (6H, s), 2.92 (3H, s), 6.71 (1H, d, J=8.3 Hz), 6.85 (1H, d, J=4.9 Hz), 7.22 (1H, d, J=7.0 Hz), 7.44 (2H, s), 7.55 (1H, dd, J=7.0 Hz, 8.3 Hz), 10.05 (1H, s)

(5-6) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide (Compound No. 2168)

N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-[N-(2,2,2-trichloroethoxycarbonyl)-N-methylamino]pyridine-2-carboxamide was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(methylamino)pyridine-2-carboxamide produced in Example 5-5 as a starting material according to the process described in Example 5-3.

¹H-NMR(DMSO-d₆, ppm) δ 2.30 (6H, s), 3.61 (3H, s), 5.03 (2H, s), 7.47 (2H, s), 7.92 (1H, d, J=7.6 Hz), 7.98 (1H, d, J=7.6 Hz), 8.08 (1H, t, J=7.6 Hz), 10.18 (1H, s)

EXAMPLE 6

(6-1) Production of ethyl 3-(2,2,2-trichloroethoxycarbonylamino)benzoate

To a solution prepared by adding 1.0 g of ethyl m-aminobenzoate and 0.72 g of pyridine to 10 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 1.55 g of 2,2,2-trichloroethyl chloroformate in 5 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 1.89 g (yield 91%) of the title compound.

¹H-NMR (CDCl₃, ppm) δ 1.40 (3H, t, J=7.3 Hz), 4.38 (2H, q, J=7.3 Hz), 4.84 (2H, s), 6.96 (1H, broad-s), 7.43 (1H, t, J=7.8 Hz), 7.76-7.82 (2H, m), 7.99 (1H, t, J=2.0 Hz)

(6-2) Production of ethyl 3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoate

To a suspension of 0.14 g of 60% sodium hydride in 5 ml of tetrahydrofuran was dropwise added a solution of 1.0 g of ethyl 3-(2,2,2-trichloroethoxycarbonylamino)benzoate in 5 ml of tetrahydrofuran, and the resultant mixture was stirred at room temperature. Then, a solution of 0.45 g of dimethyl sulfate in 5 ml of tetrahydrofuran was dropwise added, and the resultant mixture was stirred at room temperature for 3 hours. After water was added to the mixture, the mixture was subjected to extraction with ethyl acetate, and an organic layer was washed twice with water and dried with anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=4:1) to obtain 0.84 g (yield 79%) of the title compound as an oily material.

¹H-NMR (CDCl₃, ppm) δ 1.40 (3H, t, J=7.1 Hz), 3.41 (3H, s), 4.39 (2H, q, J=7.1 Hz), 4.77 (2H, s), 7.43-7.52 (2H, m), 7.93-8.01 (2H, m)

(6-3) Production of 3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoic acid

To 5 ml of ethanol were added 0.5 g of ethyl 3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoate and a 1N sodium hydroxide aqueous solution, and the resultant mixture was stirred at room temperature for 1.5 hours. After the reaction solution was controlled to pH 3 by dropwise adding 1N hydrochloric acid, ethyl acetate was added to the reaction solution, and an organic layer was separated. The organic layer was washed with water twice and washed with a saturated saline solution once, and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.45 g (yield 98%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 3.43 (3H, s), 4.79 (2H, s), 7.41-7.60 (2H, m), 7.93-8.05 (2H, m)

(6-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N′-methyl-N′-(2,2,2-trichloroethoxycarbonyl)amino]benzamide (Compound No. 1958)

A solution of 0.30 g of 3-[N-methyl-N-(2,2,2-trichloroethoxycarbonyl)amino]benzoic acid and 0.07 g of N-methylmorpholine in 5 ml of tetrahydrofuran was stirred under cooling at −15° C. A solution of 0.09 g of isopropyl chloroformate in 5 ml of tetrahydrofuran was dropwise added to the solution, and then a solution of 0.20 g of 2,6-dimethyl-4-heptafluoroisopropylaniline in 5 ml of tetrahydrofuran was dropwise added to the resultant mixture. Then, the resultant mixture was stirred at −15° C. for 1 hour and at room temperature for 24 hours. After the temperature was returned to room temperature, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was washed with water twice and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 to 2:1) to obtain 0.05 g (yield 5%) of the title compound as an oily material.

¹H-NMR (CDCl₃, ppm) δ 2.34 (6H, s), 3.45 (3H, s), 4.80 (2H, s), 7.36 (2H, s), 7.50-7.56 (3H, m), 7.78 (1H, d, J=6.1 Hz), 7.90(1H, s)

EXAMPLE 7

(7-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-iodo-5-aminobenzamide

To a solution prepared by adding 0.70 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide produced in Example 1-2 to 8 ml of N,N-dimethylformamide and then stirring the resultant mixture in an iced water bath was dropwise added a solution of 0.39 g of N-iodosuccinimide in 2 ml of N,N-dimethylformamide. After the dropwise addition, the temperature was returned to room temperature, and then mixture was further stirred for 3 hours. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:2) to obtain 0.67 g (yield 73%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.44 (6H, s), 3.86 (2H, broad-s), 6.52 (1H, dd, J=2.9 Hz, 8.5 Hz), 6.91 (1H, d, J=2.9 Hz), 7.12 (1H, s), 7.35 (2H, s), 7.62 (1H, d, J=8.5 Hz)

(7-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-iodo-5-(isopropyloxycarbonylamino)benzamide (Compound No. 1945)

To a solution obtained by adding 0.20 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-iodo-5-aminobenzamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran and then stirring the mixture at room temperature was dropwise added a solution of 0.05 g of isopropyl chloroformate in 1 ml of tetrahydrofuran. After reaction for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.22 g (yield 96%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 1.31 (6H, d, J=6.3 Hz), 2.45 (6H, s), 5.03 (1H, septet, J=6.3 Hz), 6.66 (1H, s), 7.16-7.21 (2H, m), 7.36 (2H, s), 7.76 (1H, s), 7.82 (1H, dd, J=2.7 Hz, 8.8 Hz)

EXAMPLE 8

(8-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-chloro-3-nitrobenzamide

First, to a solution prepared by adding 2.50 g of 2-chloro-3-nitrobenzoic acid and 5 droplets of N,N-dimethylformamide to 30 ml of toluene was added 1.62 g of thionyl chloride, and the resultant mixture was stirred under heating at 80° C. for 2 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of tetrahydrofuran. The resultant solution was dropwise added to a solution of 3.24 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 1.77 g of pyridine in 20 ml of tetrahydrofuran at room temperature, and the mixture was stirred for 5 hours. Then, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 3.38 g (yield 64%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.42 (6H, s), 7.34 (1H, s), 7.37 (1H, s), 7.55 (1H, t, J=7.8 Hz), 7.80 (1H, dd, J=1.5 Hz, 7.8 Hz), 7.86 (1H, dd, J=1.5 Hz, 7.8 Hz), 9.58 (1H, s)

(8-2) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-nitrobenzamide

To 25 ml of N,N-dimethylformamide dried with molecular sieve were added 2.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-chloro-3-nitrobenzamide and 0.87 g of potassium fluoride (spray-dried), and the resultant mixture was stirred under heating at 150° C. for 3 hours. After the temperature was returned to room temperature, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated, washed with water twice, and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=4:1) to obtain 1.02 g (yield 45%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.37 (6H, s), 7.39 (2H, s), 7.48-7.53 (1H, m), 7.87 (1H, d, J=11.5 Hz), 8.23-8.28 (1H, m), 8.42-8.46 (1H, m)

(8-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-aminobenzamide

The title compound was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-nitrobenzamide produced in Example 8-2 as a starting material according to the same process as in Example 1-2 (yield 72%).

¹H-NMR (CDCl₃, ppm) δ 2.37 (6H, s), 3.90 (2H, broad-s), 6.96-7.01 (1H, m), 7.10 (1H, t, J=7.8 Hz), 7.36 (2H, s), 7.43-7.47 (1H, m), 7.86 (1H, d, J=13.2 Hz)

(8-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-(isopropyloxycarbonylamino)benzamide (Compound No. 1389)

The title compound was produced by using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-aminobenzamide produced in Example 8-3 as a starting material according to the same process as in Example 7-2 (yield 72%).

¹H-NMR (CDCl₃, ppm) δ 1.34 (6H, d, J=6.3 Hz), 2.36 (6H, s), 5.07 (1H, septet, J=6.3 Hz), 6.86 (1H, broad-s), 7.30 (1H, t, J=8.1 Hz), 7.37 (2H, s), 7.72-7.79 (2H, m), 8.32 (1H, broad)

EXAMPLE 9

(9-1) Production of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoic acid

To an aqueous solution (200 ml) of 8.22 g of m-aminobenzoic acid and 4.8 g of sodium hydroxide was dropwise added 25.0 g of 2,2,2-trichloroethyl chloroformate at room temperature. During the dropwise addition, the reaction solution was controlled to pH 10 or more by appropriately adding a 1N sodium hydroxide aqueous solution. After the reaction, the solution was controlled to pH 1 by adding 1N hydrochloric acid, and the precipitates were collected by filtration. The resultant crude crystals were dried and then washed with a ethyl acetate/n-hexane mixed solvent to obtain 16.2 g (yield 87%) of the title compound as a solid.

¹H-NMR (DMSO-d₆, ppm) δ 4.85 (2H, s), 7.38 (1H, d, J=7.8 Hz), 7.75 (1H, d, J=7.8 Hz), 7.79-7.80 (1H, m), 8.14 (1H, s), 9.02 (1H, s)

(9-2) Production of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl chloride

To a toluene solution (10 ml) of 1.0 g of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoic acid produced in Example 9-1 was added 2 ml of thionyl chloride, and the resultant mixture was stirred at 100° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in toluene. The solvent was again distilled off under reduced pressure to obtain 1.0 g (yield 95%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 4.86 (2H, s), 7.00 (1H, broad-s), 7.51 (1H, t, J=7.8 Hz), 7.84 (1H, d, J=7.8 Hz), 7.88 (1H, d, J=7.8 Hz), 8.16 (1H, s)

(9-3) Production of N-(2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 3-[(2,2,2-trichloroethoxy)carbonylamino]benzamide (Compound No. 257) First, to a solution prepared by adding 0.34 g of 2,6-dimethyl-4-(nonafluoro-2-butyl)aniline and 0.09 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was added 0.33 g of 3-[(2,2,2-trichloroethoxy)carbonylamino]benzoyl chloride produced in Example 9-2. After reaction for 5 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.45 g (yield 71%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.34 (6H, s), 4.85 (2H, s), 7.10 (1H, s), 7.34 (2H, s), 7.47-7.51 (2H, m), 7.63-7.67 (2H, m), 8.05 (1H, s)

The following compounds were produced according to the processes described in Examples 9-1 and 9-2.

-   3-(ethoxycarbonylamino)benzoyl chloride -   3-(isopropylpropyloxycarbonylamino)benzoyl chloride -   3-[(cyclobutyloxy)carbonylamino]benzoyl chloride -   3-[(cyclopentyloxy)carbonylamino]benzoyl chloride -   3-[(3-cyanobenzyloxy)carbonylamino]benzoyl chloride -   3-[(4-cyanobenzyloxy)carbonylamino]benzoyl chloride -   3-[(2-cyanoethoxy)carbonylamino]benzoyl chloride -   3-[(2-methylthioethoxy)carbonylamino]benzoyl chloride -   3-[(2-ethylthioethoxy)carbonylamino]benzoyl chloride -   3-[(2-ethylsulfinylethoxy)carbonylamino]benzoyl chloride -   3-[(2-fluoroethoxy)carbonylamino]benzoyl chloride -   3-[(2,2-difluoroethoxy)carbonylamino]benzoyl chloride -   3-[(2,2,2-trifluoroethoxy)carbonylamino]benzoyl chloride -   3-[(1,3-difluoro-2-propyloxy)carbonylamino]benzoyl chloride -   3-[(1-chloro-3-fluoro-2-propyloxy)carbonylamino]benzoyl chloride -   3-[(3,3,3-trifluoro-n-propyloxy)carbonylamino]benzoyl chloride -   3-[(2,2,3,3,3-pentafluoro-n-propyloxy)carbonylamino]benzoyl chloride -   3-[(4,4,4-trifluoro-n-butyloxy)carbonylamino]benzoyl chloride -   3-[(2,2,3,3-tetrafluorocyclobutyloxy)carbonylamino]benzoyl chloride -   3-[(2-chloroethoxy)carbonylamino]benzoyl chloride -   3-[(2,2-dichloroethoxy)carbonylamino]benzoyl chloride -   3-[(1,3-dichloro-2-propyloxy)carbonylamino]benzoyl chloride -   3-[(3-chloro-n-propyloxy)carbonylamino]benzoyl chloride -   3-[(2-bromoethoxy)carbonylamino]benzoyl chloride -   3-[(3-bromo-n-propyloxy)carbonylamino]benzoyl chloride -   3-[(2-iodoethoxy)carbonylamino]benzoyl chloride -   3-[(6-chloropyridine-3-yl)methoxycarbonylamino]benzoyl chloride

EXAMPLE 10

(10-1) Production of N-(2,4-bistrifluoromethylphenyl)3-isocyanatobenzamide

To a 1,4-dioxane solution (20 ml) of 0.57 g of phosgene dimmer was added a 1,4-dioxane solution (5 ml) of 2.0 g of N-(2,4-bistrifluoromethylphenyl) 3-aminobenzamide (produced by using 2,4-bistrifluoromethylaniline as a starting material according to the process described in Example 1-2), and the resultant mixture was stirred at 60° C. for 3 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 10 ml of 1,4-dioxane. Then, the solvent was again distilled off under reduced pressure. The product was washed with n-hexane and filtered off to obtain 1.54 g (yield 72%) of the title compound.

¹H-NMR (CDCl₃, ppm) δ 7.33-7.36 (1H, m), 7.51 (1H, t, J=7.8 Hz), 7.62-7.65 (2H, m), 7.88-7.92 (2H, m), 8.31 (1H, broad-s), 8.70 (1H, d, J=8.8 Hz)

(10-2) Production of N-(2,4-bistrifluoromethylphenyl)3-[(2,2,3,3,3-pentafluoro-n-propyloxy)carbonylamino]benzamide (Compound No. 250)

First, to an anhydrous tetrahydrofuran solution (15 ml) of 0.5 g of N-(2,4-bistrifluoromethylphenyl)3-isocyanatobenzamide produced in Example 10-1 were added 0.40 g of 2,2,3,3,3-pentafluoro-n-propanol and 0.13 g of triethylamine, and the resultant mixture was stirred at room temperature for 5 hours. The mixture was diluted with ethyl acetate (20 ml), and an organic layer was washed with a 1N sodium hydroxide aqueous solution and 1N hydrochloric acid. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.49 g (yield 70%) of the title compound.

¹H-NMR (CDCl₃, ppm) δ 4.68 (2H, t, J=13.2 Hz), 7.08 (1H, broad-s), 7.50-7.59 (2H, m), 7.70 (1H, broad-s), 7.87-7.92 (2H, m), 8.00 (1H, s), 8.39 (1H, s), 8.71 (1H, d, J=8.8 Hz)

EXAMPLE 11

(11-1) Production of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzyloxycarbonyl)benzamide

A mixture of 3.24 g of benzyl alcohol and 2.85 g of pyridine was dropwise added to a tetrahydrofuran solution (60 ml) of 6.09 g of isophthaloyl chloride at room temperature. After the resultant mixture was stirred for 2 hours, a tetrahydrofuran solution (10 ml) of 2,6-dimethyl-4-heptafluoroisopropylaniline was added to the mixture in an ice bath, followed by stirring at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate (50 ml), and an organic layer was washed with 1N hydrochloric acid. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane ethyl acetate=9:1) to obtain 9.5 g (yield 60%) of the title compound as an amorphous material.

¹H-NMR (CDCl₃, ppm) δ 2.33 (6H, s), 5.41 (2H, s), 7.34-7.48 (7H, m), 7.56 (1H, s), 7.61 (1H, t, J=7.8 Hz), 8.17 (1H, t, J=7.8 Hz), 8.28 (1H, d, J=7.8 Hz), 8.57 (1H, s)

(11-2) Production of 3-[(2,6-dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic acid

Catalytic hydrogen reduction was performed at normal pressure by using a methanol solution (20 ml) of 2.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzyloxycarbonyl)benzamide produced in Example 11-1 and 0.2 g of 10% palladium-carbon (wet, 50% product) to produce 1.59 g (yield 96%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.36 (6H,s), 7.37 (2H,s), 7.59 (1H,s), 7.67 (1H, t, J=7.8 Hz), 8.23 (1H, d, J=7.8 Hz), 8.32 (1H, d, J=7.8 Hz), 8.62 (1H, s)

(11-3) Production of N-(2,6-dimethyl-4-heptafluoroisopropylphenyl) 3-isocyanatobenzamide

First, to an acetone solution (25 ml) of 1.4 g of -[(2,6-dimethyl-4-heptafluoroisopropylphenyl)aminocarbonyl]benzoic acid produced in Example 11-2 and 0.38 g of triethylamine was added 0.44 g of ethyl chloroformate in an iced water bath, and the resultant mixture was stirred at room temperature for 1 hour. Then, an aqueous solution (10 ml) of 0.32 g of sodium azide was added to the mixture, followed by stirring at room temperature for 2 hours. The reaction solution was poured into iced water (150 ml), and the precipitates were extracted with ethyl acetate (50 ml) and then dried with anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off, toluene (50 ml) was added to the filtrate, and the low-boiling-point solvent was distilled off by heating to 110° C. using a Dean and Stark tube. After the end of gas generation was confirmed, the temperature was returned to room temperature, and then the residual solvent was distilled off under reduced pressure to obtain 1.23 g (yield 88%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.35 (6H, s), 7.32 (1H, d, J=7.8 Hz), 7.37 (2H,s), 7.39 (1H,s), 7.49 (1H, t, J=7.8 Hz), 7.67 (1H,s), 7.72 (1H, d, J=7.8 Hz)

(11-4) Production of N-(2,6-dimethyl-4-heptafluoroisopropylphenyl) 3-[(1-chloro-3-trifluoromethyl-2-propyl)oxycarbonylamino]benzamide (Compound No. 120)

The title compound was produced by using N-(2,6-dimethyl-4-heptafluoroisopropylphenyl) 3-isocyanatobenzamide produced in Example 11-3 according to the process described in Example 10-2.

¹H-NMR (CDCl₃, ppm) δ 2.35 (6H, s), 3.75-3.83 (2H, m), 4.46-4.80 (2H, m), 5.19-5.24 (1H,m), 6.97 (1H, broad-s), 7.36 (2H, s), 7.36-7.48 (2H, m), 7.60-7.66 (2H, m), 8.03 (1H, s)

The following compounds were produced according to the processes described in Examples 10 and 11.

-   N-2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl 3-isocyanatobenzamide -   N-2,6-dimethyl-4-[(heptafluoro-n-propyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dibromo-4-[(heptafluoro-n-propyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dichloro-4-[(heptafluoro-n-propyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dimethyl-4-[(heptafluoroisopropyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dibromo-4-[(heptafluoroisopropyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dichloro-4-[(heptafluoroisopropyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dimethyl-4-[(nonafluoro-2-butyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dibromo-4-[(nonafluoro-2-butyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dichloro-4-[(nonafluoro-2-butyl)thio]phenyl     3-isocyanatobenzamide -   N-2,6-dimethyl-4-[(heptafluoro-n-propyl)sulfinyl]phenyl     3-isocyanatobenzamide -   N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfinyl]phenyl     3-isocyanatobenzamide -   N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfinyl]phenyl     3-isocyanatobenzamide -   N-2,6-dimethyl-4-[(heptafluoro-n-propyl)sulfonyl]phenyl     3-isocyanatobenzamide -   N-2,6-dibromo-4-[(heptafluoro-n-propyl)sulfonyl]phenyl     3-isocyanatobenzamide -   N-2,6-dichloro-4-[(heptafluoro-n-propyl)sulfonyl]phenyl     3-isocyanatobenzamide

EXAMPLE 12

(12-1) Production of 4-(heptafluoro-n-propylthio)aniline

To an acetonitrile solution (20 ml) of 4-aminothiophenol (1.25 g, 9.98 mmol) and triethylamine (1.11 g, 11.0 mmol) was added 1-iodoheptafluoro-n-propane (5.91 g, 19.9 mmol), and the resultant mixture was stirred at room temperature for 3 hours. The mixture was diluted with ether, and washed with a 1N sodium hydroxide aqueous solution. Then, the product was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.85 g (yield 63%) of the title compound.

¹H-NMR (CDCl₃, ppm) δ 3.95 (2H, s), 6.66 (2H, d, J=8.8 Hz), 7.40 (2H, d, J=8.8 Hz)

(12-2) Production of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline

First, to a solution of 0.77 g of 4-(heptafluoro-n-propylthio)aniline produced in Example 12-1 in 15 ml of N,N-dimethylformamide was added 0.98 g of N-bromosuccinimide. After the resultant mixture was stirred at 60° C. for 2 hours, ether and water were added to the mixture. Then, an organic layer was separated, washed with water twice and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=9:1) to obtain 1.19 g (yield 100%) of the title compound as a red oily material.

¹H-NMR (CDCl₃, ppm) δ 4.98 (2H, broad-s), 7.66 (2H, s)

(12-3) Production of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide

To a solution prepared by adding 1.08 g of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline produced in Example 12-2 and 0.4 g of pyridine to 20 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.55 g of 3-nitrobenzoyl chloride in 20 ml of tetrahydrofuran. After the resultant mixture was stirred at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.86 g (yield 48%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 7.73 (1H, s, J=7.8 Hz, 7.77 (1H, t, J=7.8 Hz), 7.96 (2H, s), 8.31 (1H, s), 8.47-8.50 (1H, m), 8.79 (1H, t, J=2.0 Hz)

(12-4) Production of N-{12,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-aminobenzamide

To a solution prepared by adding 0.97 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide produced in Example 12-3 and 0.95 g of tin(II) chloride (anhydrous) to 20 ml of ethanol and stirring the resultant mixture at room temperature was added 2 ml of conc. hydrochloric acid, and the resultant mixture was stirred under heating at 60° C. for 1 hour. After the temperature was returned to room temperature, the reaction solution was poured into water, and the solution was neutralized with potassium carbonate. Then, ethyl acetate was added to the solution, and insoluble materials were filtered off. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 0.75 g (yield 81%) of the title compound as a white solid.

¹H-NMR (CDCl₃, ppm) δ 3.89 (2H, broad-s), 6.90 (1H, dt, J=2.5 Hz, 6.4 Hz), 7.28-7.30 (3H, m), 7.60 (1H, s), 7.93 (2H, s)

(12-5) Production of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzamide (Compound No. 612)

To a solution prepared by adding 0.10 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-aminobenzamide and 0.02 g of pyridine to 5 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 0.04 g of 2,2,2-trichloroethyl chloroformate in 1 ml of tetrahydrofuran. After reaction for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.11 g (yield 84%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 4.86 (2H, s), 7.45 (1H, t, J=7.8 Hz), 7.72 (1H, d, J=7.8 Hz), 7.93 (2H, s), 7.94 (1H, broad-s), 8.13 (1H, s), 9.02 (1H, s), 9.17 (1H, s)

(12-6) Production of N-{2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)}phenyl 3-nitrobenzamide and N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)}phenyl 3-nitrobenzamide

A solution prepared by adding 0.5 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide to 15 ml of chloroform was stirred at room temperature, and 0.5 g of m-chloroperbenzoic acid was added to the mixture. After the resultant mixture was stirred at room temperature for 1 week, an aqueous solution of sodium hydrogen sulfite was added to the mixture, followed by stirring. Then, an organic layer was separated and washed with a 1N sodium hydroxide aqueous solution and saturated saline water. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.21 g of N-({2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)}phenyl 3-nitrobenzamide and 0.12 g of N-{2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)}phenyl 3-nitrobenzamide as solids.

(sulfinyl compound) ¹H-NMR (CDCl₃, ppm) δ 7.76-7.82 (2H, m), 8.06 (1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m), 8.49-8.53 (1H, m), 8.81 (1H, s)

(12-7) Production of 2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline

To 20 ml of DMF were added 3.0 g (1.3 mmol) of 2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmol) of potassium carbonate, 0.75 g (0.65 mmol) of tetrakis(triphenylphosphine) palladium, and 0.17 g (1.3 mmol) of trimethylboroxine, and the resultant mixture was stirred at 135° C. for 6 hours. After the reaction solution was cooled to room temperature, insoluble materials were filtered off with cerite. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=12:1 to 4:1) to obtain 1.17 g (yield 55%) of the title compound as an oily material.

¹H-NMR (CDCl₃, ppm) δ 2.17 (6H,s), 3.86 (2H, broad-s), 7.22 (2H, s)

The following aniline derivatives can be produced according to the processes described in Examples 12-1, 12-2, 12-6, and 12-7.

-   2-methyl-4-(pentafluoroethylthio)aniline -   2-methyl-4-(heptafluoro-n-propylthio) aniline

¹H-NMR (CDCl₃, ppm) δ 2.16 (3H, s), 3.90 (2H, broad-s), 6.65 (1H, d, J=8.3 Hz), 7.28-7.31 (2H, m)

-   2-bromo-4-(heptafluoro-n-propylthio)aniline

¹H-NMR (CDCl₃, ppm) δ 4.44 (2H, broad-s), 6.75 (1H, d, J=8.8 Hz), 7.36 (1H, dd, J=2.0 Hz, 8.8 Hz), 7.69 (1H, d, J=2.0 Hz)

-   2-methyl-4-(heptafluoroisopropylthio)aniline -   2-methyl-4-(nonafluoro-n-butylthio)aniline -   2-methyl-4-(pentafluoroethylsulfinyl)aniline -   2-methyl-4-(heptafluoro-n-propylsulfinyl)aniline -   2-methyl-4-(heptafluoroisopropylsulfinyl) aniline -   2-methyl-4-(nonafluoro-n-butylsulfinyl)aniline -   2-methyl-4-(pentafluoroethylsulfonyl)aniline -   2-methyl-4-(heptafluoro-n-propylsulfonyl)aniline -   2-methyl-4-(heptafluoroisopropylsulfonyl) aniline -   2-methyl-4-(nonafluoro-n-butylsulfonyl)aniline -   2,6-dichloro-4-(pentafluoroethylthio)aniline -   2,6-dibromo-4-(pentafluoroethylthio)aniline -   N-{2,6-dibromo-4-(pentafluoroethylthio)}phenyl 3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.73 (1H,s), 7.77 (1H, t, J=7.8 Hz), 7.96 (2H, s), 8.32 (1H, d, J=7.8 Hz), 8.47-8.50 (1H, m), 8.80 (1H, t, J=2.0 Hz)

-   2,6-dimethyl-4-(pentafluoroethylthio)aniline -   2,6-dichloro-4-(heptafluoro-n-propylthio)aniline

¹H-NMR (CDCl₃, ppm) δ 4.82 (2H, broad-s), 7.48 (2H, s)

-   N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.70 (1H, s), 7.76 (2H, s), 7.77 (1H, t, J=7.8 Hz), 8.31 (1H, d, J=7.8 Hz), 8.48 (1H, d, J=7.8 Hz), 8.78 (1H, t, J=2.0 Hz)

-   2,6-dibromo-4-(heptafluoro-n-propylthio)aniline

¹H-NMR (CDCl₃, ppm) δ 4.93 (2H, broad-s), 7.66 (2H, s)

-   2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline

¹H-NMR (CDCl₃, ppm) δ 2.17 (6H, s), 3.86 (2H, broad-s), 7.22 (2H, s)

-   N-{2,6-dichloro-4-(heptafluoro-n-propylthio)}phenyl     2-chloro-3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 2.39 (6H, s), 7.30 (1H, s), 7.46 (2H, s), 7.57 (1H, t, J=7.8 Hz), 7.90 (1H, d, J=7.8 Hz), 7.91 (1H, d, J=7.8 Hz)

-   2-bromo-4-(heptafluoro-n-propyl)thio-6-methylaniline

¹H-NMR (CDCl₃, ppm) δ 2.22 (3H, s), 4.40 (2H, broad-s), 7.27 (1H, s), 7.60 (1H, d, J=2.0 Hz)

-   2,6-dichloro-4-(heptafluoroisopropylthio)aniline

¹H-NMR (CDCl₃, ppm) δ 6.40 (2H, s), 7.52 (2H, s)

-   2,6-dibromo-4-(heptafluoroisopropylthio)aniline -   N-{2,6-dichloro-4-(heptafluoroisopropylthio)}phenyl 3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.73 (1H, s), 7.76 (1H, t, J=7.8 Hz), 7.95 (2H, s), 8.31 (1H, d, J=7.8 Hz), 8.48 (1H, d, J=7.8 Hz), 8.79 (1H, t, J=1.5 Hz)

-   2,6-dimethyl-4-(heptafluoroisopropylthio)aniline -   2,6-dichloro-4-(nonafluoro-n-butylthio)aniline -   2,6-dibromo-4-(nonafluoro-n-butylthio)aniline -   N-{2,6-dichloro-4-(nonafluoro-n-butylthio)}phenyl 3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.76 (1H,s), 7.77 (1H, t, J=8.3 Hz), 7.96 (2H, s), 8.32 (1H, d, J=8.3 Hz), 8.48 (1H, d, J=8.3 Hz), 8.80 (1H, t, J=2.0 Hz)

-   2,6-dimethyl-4-(nonafluoro-n-butylthio)aniline -   2,6-dichloro-4-(pentafluoroethylsulfinyl)aniline -   2,6-dibromo-4-(pentafluoroethylsulfinyl)aniline -   2,6-dimethyl-4-(pentafluoroethylsulfinyl)aniline -   2,6-dichloro-4-(heptafluoro-n-propylsulfinyl)aniline -   2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)aniline -   N-{2,6-dichloro-4-(heptafluoro-n-propylsulfinyl)}phenyl     3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.76-7.82 (2H, m), 8.06(1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m), 8.49-8.53 (1H, m), 8.81(1H, s)

-   2,6-dimethyl-4-(heptafluoro-n-propylsulfinyl)aniline -   2,6-dichloro-4-(heptafluoroisopropylsulfinyl)aniline -   2,6-dibromo-4-(heptafluoroisopropylsulfinyl)aniline -   2,6-dimethyl-4-(heptafluoroisopropylsulfinyl)aniline -   2,6-dichloro-4-(nonafluoro-n-butylsulfinyl)aniline -   2,6-dibromo-4-(nonafluoro-n-butylsulfinyl)aniline -   2,6-dimethyl-4-(nonafluoro-n-butylsulfinyl)aniline -   2,6-dichloro-4-(pentafluoroethylsulfonyl)aniline -   2,6-dibromo-4-(pentafluoroethylsulfonyl)aniline -   2,6-dimethyl-4-(pentafluoroethylsulfonyl)aniline -   2,6-dichloro-4-(heptafluoro-n-propylsulfonyl)aniline -   2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)aniline -   2,6-dimethyl-4-(heptafluoro-n-propylsulfonyl)aniline -   2,6-dichloro-4-(heptafluoroisopropylsulfonyl)aniline -   N-{2,6-dichloro-4-(heptafluoroisopropylsulfonyl)}phenyl     3-nitrobenzamide

¹H-NMR (CDCl₃, ppm) δ 7.79 (1H, t, J=7.8 Hz), 7.98 (1H, s), 8.07 (2H, s), 8.33 (1H, d, J=7.8 Hz), 8.51 (1H, d, J=7.8 Hz), 8.81 (1H, t, J=2.0 Hz)

-   2,6-dibromo-4-(heptafluoroisopropylsulfonyl)aniline -   2,6-dimethyl-4-(heptafluoroisopropylsulfonyl)aniline -   2,6-dichloro-4-(nonafluoro-n-butylsulfonyl)aniline -   2,6-dibromo-4-(nonafluoro-n-butylsulfonyl)aniline -   2,6-dimethyl-4-(nonafluoro-n-butylsulfonyl)aniline

EXAMPLE 13

(13-1) Production of 2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline

A mixture of 2.42 g of 2,6-dimethylaniline, 7.35 g of hexafluoroacetone hydrate, and 0.04 g of p-toluenesulfonic acid monohydrate was stirred under heating at 100° C. for 5 hours. After the temperature was returned to room temperature, the mixture was diluted with ethyl acetate and washed with a 1N sodium hydroxide aqueous solution. Then, the solvent was distilled off under reduced pressure, and the precipitated crude crystals were washed with a n-hexane-ethyl acetate mixed solvent to obtain 4.47 g (yield 78%) of the title compound as a solid.

¹H-NMR (CDCl₃, ppm) δ 2.20 (6H, s), 3.26 (1H, broad-s), 3.76 (2H, broad-s), 7.25 (2H, s)

(13-2) Production of N-[2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)]phenyl 3-(2,2,2-trichloroethoxycarbonylamino)benzamide (Compound No. 872)

The title compound was produced as an amorphous material by using 2,6-dimethyl-4-(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl)aniline produced in Example 13-1 as a starting material according to the process described in Example 9-3 (yield 92%).

¹H-NMR (CDCl₃, ppm) δ 2.31 (6H, s), 3.99 (1H, s), 4.85 (2H, s), 7.15 (1H, broad-s), 7.45-7.51 (4H, m), 7.64-7.66 (2H, m), 8.01 (1H, s)

Formulation examples containing the compounds represented by formula (1) of the present invention as active ingredients are shown below, however the present invention is not limited to these examples. In each of the formulation examples, “part(s)” represents “part(s) by weight”.

FORMULATION EXAMPLE 1

A mixture of 20 parts of a compound represented by formula (1) of the present invention, 10 parts of Sorpol 355S (surfactant produced by Toho Chemical Industry Co., Ltd.), and 70 parts of xylene was uniformly stirred to produce an emulsion.

FORMULATION EXAMPLE 2

A mixture of 10 parts of a compound represented by formula (1) of the present invention, 2 parts of sodium alkylnaphthalenesulfonate, 1 part of sodium lignin-sulfonate, 5 parts of white carbon, and 82 parts of diatomite was uniformly stirred to produce a wettable powder.

FORMULATION EXAMPLE 3

A mixture of 0.3 parts of a compound represented by formula (1) of the present invention and 0.3 parts of white carbon was uniformly stirred, and 99.2 parts of clay and 0.2 parts of Driless A (produced by Sankyo Co., Ltd.) were added to the mixture. The resultant mixture was uniformly ground to produce a dust.

FORMULATION EXAMPLE 4

A mixture of 2 parts of a compound represented by formula (1) of the present invention, 2 parts of white carbon, 2 parts of sodium lignin-sulfonate, and 94 parts of bentonite was uniformly ground, and then water was added to the mixture. The resultant mixture was kneaded, granulated and then dried to produce granules.

FORMULATION EXAMPLE 5

A mixture of 20 parts of a compound represented by formula (1) of the present invention and 5 parts of a 20% aqueous solution of polyvinyl alcohol was sufficiently stirred, and then 75 parts of a 0.8% aqueous solution of xanthane gum was added to the mixture. Then, the resultant mixture was again stirred to produce a flowable agent.

Test examples for making clear that the compounds represented by formula (1) of the present invention have excellent insecticidal activity are shown below, however the present invention is not limited to these examples.

TEST EXAMPLE 1 Insecticidal Test for Common Cutworm (Spodoptera litura)

A cabbage leaf piece was immersed in a solution prepared by diluting a test compound to a predetermined concentration for 30 seconds, and then dried in air. Then, the cabbage leaf piece was placed in a polyethylene cup of 7 cm-size in which 2nd-instar larvae of common cutworm were placed. The cup was allowed to stand in a thermostatic chamber at 25° C. Three days after, the numbers of living and dead larvae were counted. The test was carried out in two replications each containing five larvae.

As a result, at a concentration of 1000 ppm, a mortality of 70% or more was exhibited by Compounds Nos. 20, 59, 60, 62, 64, 66, 75, 78, 79, 81, 83, 84, 85, 90, 91, 92, 106, 108, 109, 111, 112, 116, 117, 118, 119, 120, 121, 123, 124, 125, 126, 127, 130, 131, 132, 134, 135, 136, 137, 138, 139, 140, 155, 156, 161, 163, 165, 174, 175, 176, 180, 181, 184, 186, 189, 190, 192, 196, 197, 198, 205, 206, 207, 208, 209, 210, 212, 213, 215, 216, 217, 218, 219, 220, 221, 224, 225, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 241, 246, 247, 248, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518, 565, 605, 612, 659, 706, 770, 800, 817, 818, 819, 854, 855, 856, 857, 843, 844, 846, 847, 864, 867, 872, 873, 878, 890, 891, 892, 898, 899, 900, 902, 903, 905, 913, 915, 916, 919, 920, 922, 932, 933, 944, 948, 992, 1010, 1039, 1086, 1104, 1180, 1198, 1227, 1245, 1274, 1292, 1321, 1361, 1368, 1388, 1389, 1408, 1411, 1416, 1418, 1421, 1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1922, 1923, 1924, 1925, 1926, 1929, 1931, 1932, 1935, 1939, 1941, 1942, 1943, 1944, 1945, 1947, 1948, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1958, 1959, 1963, 1964, 1967, 1968, 1969, 2061, 2062, 2164, 2165, and 2168.

TEST EXAMPLE 2 Insecticidal Test for Diamondback Moth (Plutella xylostella)

A cabbage leaf pieces was immersed in a solution prepared by diluting a test compound to a predetermined concentration for 30 seconds, and then dried in air. Then, the leaf piece was placed in a polyethylene cup of 7 cm-size in which 2nd-instar larvae of common cutworm were placed. The cup was allowed to stand in a thermostatic chamber at 25° C. Three days after, the numbers of living and dead larvae were counted. The test was carried out in two replications each containing five larvae.

As a result, at a concentration of 1000 ppm, a mortality of 70% or more was exhibited by Compounds Nos. 3, 5, 7, 8, 20, 59, 60, 62, 66, 75, 77, 78, 79, 80, 84, 85, 92, 94, 95, 96, 99, 101, 103, 104, 106, 108, 109, 110, 111, 112, 113, 116, 117, 118, 119, 120, 121, 123, 126, 127, 130, 131, 132, 134, 136, 137, 138, 139, 140, 141, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 168, 171, 174, 175, 176, 180, 181, 183, 184, 186, 190, 192, 196, 197, 198, 201, 203, 204, 205, 206, 207, 208, 209, 212, 213, 214, 215, 217, 218, 219, 220, 221, 223, 224, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 246, 247, 248, 249, 250, 252, 253, 254, 255, 256, 257, 258, 259, 300, 301, 348, 377, 424, 464, 471, 511, 518, 565, 605, 612, 659, 706, 800, 817, 818, 819, 820, 829, 858, 863, 865, 867, 868, 871, 872, 873, 878, 896, 897, 898, 899, 900, 902, 908, 913, 915, 919, 920, 922, 930, 932, 933, 936, 939, 941, 942, 943, 944, 945, 947, 948, 992, 1010, 1039, 1086, 1104, 1180, 1227, 1245, 1274, 1292, 1321, 1361, 1368, 1388, 1389, 1408, 1411, 1416, 1418, 1421, 1435, 1455, 1458, 1463, 1465, 1903, 1906, 1907, 1916, 1923, 1926, 1928, 1929, 1931, 1933, 1939, 1945, 1947, 1950, 1951, 1952, 1953, 1954, 1955, 1956, 1958, 1959, 1963, 1964, 1967, 1968, 1969, 2061, 2062, 2164, 2165, 2167, and 2168.

TEST EXAMPLE 3 Insecticidal Test for Small Brown Planthopper (Laodelphax striatellus)

An acetone solution prepared by diluting a test compound to a predetermined concentration was sprayed on rice seedlings, and the rice seedlings were dried in air. Ten small brown planthoppers and an original chemical were used for the test. The rice seedlings were allowed to stand in a thermostatic chamber at 25° C. Six days after, the number of living insects was examined, and three days after, the number of dead insects was examined. The test was carried out one replication containing ten insects.

As a result, at a concentration of 1000 ppm, a mortality of 70% or more was exhibited by Compounds Nos. 108, 127, 184, 196, 197, 205, 209, 212, 215, 1321, 1361, 1368, 1408, 1411, 1416, 1435, 1455, 1458, 1463, 1958, 1959, and 1968. 

1. A compound represented by formula (1):

wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₁ represents a C1-C6 alkyl group which may be substituted, a phenyl group which may be substituted, a naphthyl group which may be substituted, or a heterocyclic group which may be substituted; R₂ and R₃ independently represent a hydrogen atom, a C1-C4 alkyl group which may be substituted, or a C1-C4 alkylcarbonyl group which may be substituted; G₁, G₂, and G₃ independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group which may be substituted, or an amino group which may be substituted; n represents an integer of 0 to 4; Q represents a phenyl group which may be substituted, a naphthyl group which may be substituted, a tetrahydronaphthyl group which may be substituted, or a heterocyclic group which may be substituted.
 2. The compound according to claim 1, wherein in formula (1), A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₁ represents: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, -E₁-Z₁-R₄ (wherein E₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group; R₄ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group); and Z₁ represents —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R₅)—, —C(═O)N(R₅)—, or —N(R₅)C(═O)— (R₅ represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, or a C1-C4 alkoxycarbonyl group)), or -E₂-R₆ (wherein E₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, and R₆ represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group); R₂ and R₃ independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G₁, G₂, and G₃ independently represent an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, an amino group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; and Q represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a phenyl group, a substituted phenyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a thienyl group, and a substituted thienyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 halo alkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a tetrahydronaphthyl group, or a substituted tetrahydronaphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group (excluding case (1) in which Q represents a 3,4-dichlorophenyl group when R1 represents a methyl group, case (2) in which Q represents an unsubstituted phenyl group when R1 represents an ethyl group, and case (3) in which Q represents an unsubstituted pyridyl group when R1 represents an unsubstituted phenyl group.)
 3. The compound according to claim 2, wherein in formula (1), G₁ and G₃ each represent an oxygen atom, and Q represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a heterocyclic group (which represents a pyridyl group or a pyrazolyl group), a substituted heterocyclic group (which represents a pyridyl group or a pyrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a tetrahydronaphthyl group, or a substituted tetrahydronaphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group.
 4. The compound according to claim 3, wherein in formula (1), Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, or a trifluoromethyl group, and n is an integer of 0 to
 4. 5. The compound according to claim 4, wherein in formula (1), R₁ represents: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, -E₁-Z₁-R₄ (wherein E₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, R₄ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, and Z, represents —O—, —S—, —SO—, or —SO₂—), or -E₂-R₆ (wherein E₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, and R₆ represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, and a pentafluorosulfanyl group, a pyridyl group, a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group, and a C1-C6 haloalkoxy group, a thienyl group, or a tetrahydrofuryl group).
 6. The compound according to claim 5, wherein in formula (1), A₁, A₂, A₃, and A₄ are all carbon atoms, or one any of A₁, A₂, A₃, and A₄ is a nitrogen atom or an oxidized nitrogen atom, and G₂ is an oxygen atom.
 7. The compound according to claim 6, wherein in formula (1), Q represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, and a nitro group; a pyridyl group, or a substituted pyridyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, and a nitro group.
 8. The compound according to claim 7, wherein in formula (1), Q is a substituent represented by formula (1-2) or (1-3):

(wherein Y₁, Y₂, Y₄, and Y₅ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₃ represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₁ and Y₅ represents a hydrogen atom)

(wherein Y₆, Y₇, and Y₉ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₈ represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₆ and Y₉ represents a hydrogen atom).
 9. A compound represented by formula (2):

wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom, and R₁ represents the following: a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 halo alkyl sulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group), or -E₁-Z₁-R₄ (wherein E₁ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group; R₄ represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group), and Z₁ represents —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R₅)—, —C(═O)N(R₅)—, or —N(R₅)C(═O)— (R₅ represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 alkoxycarbonyl group)), or -E₂-R₆ (wherein E₂ represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group, or a C3-C4 haloalkynylene group, and R₆ represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxyl group, a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), or a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a tetrahydropyranyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, and a C1-C4 alkoxycarbonyl group); R₂ represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G₁, G₂, and G₃ independently represents an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; and Hal represents a halogen atom (excluding a case in which R1 is an unsubstituted benzyl group when X is a hydrogen atom.}
 10. A compound represented by formula (3):

wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₃ represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G₃ represents an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; and Q represents a phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a cyano group, a nitro group, a hydroxyl group, a pentafluorosulfanyl group, a phenyl group, a substituted phenyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a thienyl group, a substituted thienyl group (which may have the same or different substituents selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 haloalkylsulfonyloxy group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group), a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyrrole group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group), a substituted heterocyclic group (which represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, an imidazolyl group, a triazolyl group, a pyrazolyl group, or a tetrazolyl group) having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group, a tetrahydronaphthyl group, or a substituted tetrahydronaphthyl group having one or more substituents which may be the same or different and which are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a cyano group, a nitro group, a hydroxyl group, and a pentafluorosulfanyl group.
 11. A compound represented by formula (4):

wherein A₁, A₂, A₃, and A₄ independently represent a carbon atom, a nitrogen atom, or an oxidized nitrogen atom; R₂ and R₃ independently represent a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, or a C1-C4 haloalkylcarbonyl group; G₃ represents an oxygen atom or a sulfur atom; Xs may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a cyano group, a nitro group, or an amino group which may be substituted by a C1-C4 alkyl group; n represents an integer of 0 to 4; and Q is a substituent represented by formula (1-2) or (1-3):

 (wherein Y₁, Y₂, Y₄, and Y₅ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₃ represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₁ and Y₅ represents a hydrogen atom);

 (wherein Y₆, Y₇, and Y₉ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C I—C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and Y₈ represents a C I—C6 haloalkyl group, a C I—C6 haloalkoxy group, a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, or a pentafluorosulfanyl group, but only one of Y₆ and Y₉ represents a hydrogen atom).
 12. A method for producing the compound according to claim 1, the method comprising reacting the compound represented by formula (2) according to claim 9 with a compound represented by formula (5):

wherein R₃ and Q each represent the same as in claim
 1. 13. A method for producing the compound according to claim 1, the method comprising reacting the compound represented by formula (3) according to claim 10 with a compound represented by formula (6): H-G₂-R₁  (6) wherein R₁ and G₂ each represent the same as in claim
 1. 14. A method for producing the compound according to claim 1, the method comprising reacting the compound represented by formula (4) according to claim 11 with a compound represented by formula (7):

wherein R₁, G₁, and G₂ each represent the same as in claim
 1. 15. An aniline derivative represented by formula (8):

wherein R₇ represents a C1-C6 haloalkyl group, Y₁₀, Y₁₁, Y₁₂, and Y₁₃ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and R₈ and R₉ independently represent a hydrogen atom, a C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted m-nitrobenzoyl group, and m represents 0, 1, or
 2. 16. An aniline derivative represented by formula (9):

wherein R₁₀ represents a C1-C6 haloalkyl group which may be substituted by at least one hydroxyl group, Y₁₄, Y₁₅, Y₁₆, and Y₁₇ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a cyano group, or a nitro group, and R₁₁ and R₁₂ independently represent a hydrogen atom, a C1-C4 alkyl group, a m-nitrobenzoyl group, or a substituted m-nitrobenzoyl group.
 17. An insecticide comprising the compound according to claim 1 as an active ingredient.
 18. An agricultural/horticultural insecticide comprising the compound according to claim 1 as an active ingredient.
 19. A method for using a chemical comprising treating a useful crop or soil with an effective amount of the compound according to claim 1, for protecting the useful crop from harmful organisms.
 20. A method for preventing pests comprising using the compound according to claim 1 and at least one fungicide and/or insecticide in combination.
 21. The method for preventing pests according to claim 20, wherein the fungicide and/or insecticide is selected from azole fungicides such as triadimefon, hexaconazole, propiconazole, ipconazole, prochloraz, and triflumizole; pyrimidine fungicides such as pyrifenox and fenarimol; anilinopyrimidine fungicides such as mepanipyrim and cyprodinil; acylalanine fungicides such as metalaxyl, oxadixyl, and benalaxyl; benzimidazole fungicides such as thiophanate-methyl and benomyl; dithiocarbamate fungicids such as mancozeb, propineb, zineb, and metiram; organochlorine fungicides such as tetrachloroisophthalonitrile; carboxamide fungicides such as carpropamid and ethaboxam; morpholine fungicides such as dimethomorph; strobilurin fungicides such as azoxystrobin, kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin; dicarboxyimide fungicides such as iprodione and procymidone; soil-applied fungicides such as flusulfamide, dazomet, methyl isothiocyanate, and chloropicrin; copper fungicides such as basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, oxine-copper, and DBEDC; inorganic fungicides such as sulfur and zinc sulfate; organophosphate fungicides such as edifenphos, tolclofos-methyl, and fosetyl-aluminum; melanin biosynthesis inhibitors such as phthalide, tricyclazole, pyroquilon, and diclocymet; antibiotics such as kasugamycin, validamycin, and polyoxins; fungicidal natural products such as repe seed oil; and other fungicides such as benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid, quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid, proquinazid, silthiofam, oxypoconazole, famoxadone, cyazofamid, fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole, chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet, dichlofluanid, (RS)—N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide(penthiopyrad; ISO proposed), oxycarboxin, mepronil, flutolanil, triforine, oxolinic acid, probenazole, acibenzolar-S-methyl, isoprothiolane, ferimzone, diclomezine, pencycuron, fluoroimide, chinomethionate, iminoctadine-triacetate, and iminoctadine-albesilate; synthetic pyrethroid insecticides such as allethrin, tetramethrin, resmethrin, phenothrin, furamethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropathrin, tralomethrin, cycloprothrin, flucythrinate, fluvalinate, acrinathrin, tefluthrin, bifenthrin, empenthrin, beta-cyfluthrin, zeta-cypermethrin, and fenvalerate, and various isomers thereof and pyrethrum extracts; organophosphate insecticides such as DDVP, cyanophos, fenthion, fenitrothion, tetrachlorvinphos, dimethylvinphos, propaphos, methylparathion, temephos, phoxim, acephate, isofenphos, salithion, DEP, EPN, ethion, mecarbam, pyridafenthion, diazinon, pirimiphos-methyl, etrimfos, isoxathion, quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet, methidathion, oxydeprofos, vamidothion, malathion, phenthoate, dimethoate, formothion, thiometon, ethylthiometon, phorate, terbufos, profenofos, prothiofos, sulprofos, pyraclofos, monocrotophos, naled, fosthiazate, and cadusafos; carbamate insecticides such as NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, ethiofencarb, bendiocarb, pirimicarb, carbosulfan, benfuracarb, methomyl, oxamyl, and aldicarb; arylpropylether insecticides such as etofenprox and halfenprox; silylether insecticides such as silafluofen; insecticidal natural products such as nicotine-sulfate, polynactin complex, abamectin, milbemectin, and BT agents; insecticides such as, cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil, buprofezin, fenoxycarb, pyriproxyfen, methoprene, hydroprene, kinoprene, diafenthiuron, triazamate, tebufenozide, and endosulfan; acaricides such as dicofol, chlorobenzilate, bromopropylate, tetradifon, CPCBS, BPPS, chinomethionate, amitraz, benzoximate, hexythiazox, fenbutatin oxide, cyhexatin, dienochlor, clofentezine, pyridaben, fenpyroximate, fenazaquin, and tebufenpyrad; novaluron; noviflumuron; emamectin benzoate; clothianidin; thiacloprid; thiamethoxam; flupyrazofos; acequinocyl; bifenazate; chromafenozide; etoxazole; fluacrypyrim; flufenzine; halofenozide; indoxacarb; methoxyfenozide; spirodiclofen; tolfenpyrad; gamma-cyhalothrin; ethiprole; amidoflumet; bistrifluron; flonicamid; flubrocythrinate; flufenerim; pyridalyl; pyrimidifen; spinosad; and spiromesifen. 